A serial rapist from Brooklyn targeted sex workers and a cleaning service worker, drugging them, robbing them and forcing two of them into sex, federal prosecutors said Wednesday.

Chad Barclay’s crime spree started last September and he’s been arrested multiple times, but has either been released without bail or paid his bond. On Wednesday, his fortune changed when a magistrate judge in Brooklyn ordered him held on federal charges in connection a Sept. 13 attack on a sex worker.

“The defendant has engaged in a dangerous criminal pattern of enticing women to meet with him for various purposes, and then proceeding to rape and rob them through the use of threatening and coercive means,” federal prosecutors wrote in a Wednesday filing.

The feds identified three attacks and said they were looking into more, “including some of which were committed within the past week.”

Barclay, 29, met the first known victim through Eros, an online escort site, and agreed to pay her $1,500 to come to Brooklyn from out of state and have sex with him, according to federal prosecutors.

She set some ground rules, including that he had to use a condom, and he agreed, the feds said.

When she showed up at his Brooklyn apartment on Sept. 1, he gave her a glass of water and she became woozy and confused, the feds allege. He repeatedly took off the condom during sex, and when she told him she didn’t consent, he forced himself on her, according to prosecutors.

He then took $2,000 cash form her, told her that he was a pimp and gang member and said she had to pay him a tax for working in Brooklyn, the feds allege.

He threatened to hurt her, saying that he had “dangerous” men working for him around the area, prosecutors added. He grabbed her phone and scrolled through its contents, telling her he knew where she lived and that she had a child, prosecutors allege.

He wouldn’t let her leave until she warned him that one of her friends knew where she was and would call the police if she didn’t check in.

The cops arrested him on Nov. 2 and charged him with third-degree robbery and other charges. Those charges weren’t bail-eligible, so he was cut loose. In February, he was indicted on rape and other charges and made his $50,000 bond.

He also robbed a woman he hired to clean his apartment on Sept. 24, telling her she couldn’t leave because he had two of “his men” outside the building that were more dangerous than him, prosecutors allege. He tried to use her phone to pay himself with Cash App and PayPal, then took her debit cards and demanded her PIN numbers, prosecutors say.

When the PIN numbers didn’t work, he came back and started slamming her fist into his palm and she gave him the correct digits — and she fled when he went to the bank, prosecutors said. He was arrested later that day and again charged with third-degree robbery but released without bail.

He’s also accused of raping and robbing a sex worker in the Bronx on May 3 after hiring her off Craigslist. Like before, he gave the woman a drink that made her feel woozy, then choked and raped her, threatening to shoot her if she called the cops, the feds allege.

He was busted that same day and ordered held on $300,000 bond. But at his next court appearance on May 9, a Bronx criminal court judge ordered him released without bail.

Unless a defendant agrees otherwise, state prosecutors must indict someone held on bail on a felony within five business days or they’re released without bail.

It’s not clear if that’s what happened in that case. The Bronx district attorney’s office did not immediately return messages seeking comment.