OAKLAND -- Police fired tear gas at least five times Tuesday night into a crowd of several hundred protesters backing the Occupy movement who unsuccessfully tried to retake an encampment outside Oakland City Hall that officers had cleared away more than 12 hours earlier.

Police gave repeated warnings to protesters to disperse from the entrance to Frank Ogawa Plaza at 14th Street and Broadway before firing several tear gas canisters into the crowd at about 7:45 p.m. Police had announced over a loudspeaker that those who refused to leave could be targeted by "chemical agents."

Protesters scattered in both directions on Broadway as the tear gas canisters and several flash-bang grenades went off. Regrouping, protesters tried to help one another and offered each other eye drops.

One wounded woman, who others said had been hit by one of the canisters, was carried away by two protesters.

One protester, 35-year-old Jerry Smith, said a tear gas canister had rolled to his feet and sprayed him in the face.

"I got the feeling they meant business, but people were not going to be intimidated," Smith said. "We can do this peacefully, but still not back down."

Police forcibly dispersed the crowd with tear gas again about 9:30 p.m., when protesters began throwing objects at them. As protesters scattered, police closed off Broadway between 13th and 16th streets.

Minutes later, protesters regrouped at the 15th Street entrance to the plaza. Protesters began throwing objects again. Police responded by firing more tear gas canisters.

Protesting eviction

The protesters were trying to make good on a vow to retake an encampment that Occupy Oakland activists had inhabited for 15 days, until police evicted them early Tuesday.

The evening protest started around 5 p.m., when about 400 people began marching from the main library at 14th and Madison streets toward the plaza, which police had barricaded and city officials had declared would be closed for at least several days.

"We're going to march and reclaim what was already ours, what we call Oscar Grant Plaza and what they call City Hall," said protester Krystof Lopaur, referring to the unarmed man shot to death by a BART police officer in January 2009.

Early on, the scene outside City Hall was largely peaceful, but it was a different story a few blocks west on Washington Street.

Officers in riot gear hemmed in protesters around 6 p.m. and attempted to arrest one person, as about 50 more surrounded them shouting, "Let him go, let him go."

Protesters threw turquoise and red paint at the riot officers. Some led the crowd in chanting, "This is why we call you pigs."

Some displeased

Others pleaded with agitators to be peaceful and return to the march; some protesters tried to fight with police and were clubbed and kicked in return.

Interim Oakland police chief Howard Jordan said his officers had no choice but to respond with tear gas. The crowd at its peak grew to more than 1,000 at about 8:30 p.m., and two officers were wounded from the paint and chemicals thrown at them.

"We felt that the deployment of the gas was necessary to protect our officers," he said at a news conference.

Although police did not provide a number of arrests in Tuesday night's demonstration, he said five people involved with the Occupy movement had been arrested earlier, after the morning raid.

Some protesters who avoided conflict and wanted to show their support for the Occupy Wall Street movement were displeased by the violent turns.

"They didn't have to force police into that situation," said Helen Walker, 46, a nurse from Albany. "It was totally provoked, and if I could have, I would have stopped those idiots from throwing paint."

Toward the end of the night, protesters continued throwing objects at officers, only to be tear gassed in return. After the fourth exchange, some demonstrators took to their bullhorns to try to stop their peers from goading the police. About 150 to 200 protesters remained at Frank Ogawa Plaza after 11 p.m., staring down the officers keeping them from entering.

While the majority of damage was limited to trash cans set on fire and a stolen traffic sign at 15th and Broadway, the worst damage of the night was when protesters smashed the back window of a California Highway Patrol cruiser.

Five-minute sweep

The confrontation came hours after police swept through Occupy Oakland's encampment outside City Hall and a second, smaller camp nearby, arresting 97 people who were protesting as part of a nationwide movement against economic inequality and corporate greed.

City officials said they had been forced to clear the encampments because of sanitary and public safety concerns.

Protesters said the arrest total was 105, and said three people had suffered injuries - one a head wound and two with broken hands. City officials said they knew of no injuries.

The police, drawn from 18 law enforcement agencies throughout the East Bay, began making arrests shortly before 5 a.m. and removing tents and makeshift shelters. Within five minutes the bulk of the arrests had been completed, and arrestees were led away in plastic handcuffs. Most were arrested for unlawful assembly and illegal lodging, police said.

At 6:15 a.m., police arrested a handful of protesters at a smaller encampment at Snow Park at 19th and Harrison streets near Lake Merritt. One man went limp, but those arrests also happened quickly and without incident amid cries of protest by onlookers yelling, "Cops! Pigs! Murderers!"

Earlier orders to vacate

Mayor Jean Quan was in Washington on a lobbying trip as the arrests were made.

"We've been trying (to talk) with the Occupy Oakland people for the last two weeks," Quan told KGO radio. "Last week it was pretty clear that there was escalating violence."

Officials initially waived city laws that ban camping and allowed the occupation of the plaza. But starting Thursday, the city issued of series of orders for protesters to vacate the area, citing concerns about fire hazards, sanitation issues, graffiti, drug use and violence.

Protesters had vowed to resist eviction and protect the encampment that had grown to about 150 tents. Pathways made of wooden pallets connected a kitchen, a garden, a medical station and an area for children to play.

Gabe Meyers, a protester who had been camping at the plaza, said, "People are going to keep coming back. What are they going to do, send cops in every night and waste taxpayer dollars?"

Meyers added, "The cops are the 99 percent, but they're doing the work of the 1 percent. Wall Street is proud of them every time they clear out an encampment."

Chronicle staff writers Henry K. Lee, Will Kane and Vivian Ho contributed to this report.