1-(4-Methoxyphenyl)-4-phenethylpiperazine → 4-(2,5-Difluoro-4-hydroxyphenyl)-1-(octylsulfonyl)piperazine

HRID 269943Notes

Reaction equation

HRID 269943 reaction equation
COC1C=CC(N2CCN(CCC3C=CC=CC=3)CC2)=CC=1.[F:23][C:24]1[CH:29]=[C:28]([O:30]C)[C:27]([F:32])=[CH:26][C:25]=1[N:33]1[CH2:38][CH2:37][N:36]([S:39]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])(=[O:41])=[O:40])[CH2:35][CH2:34]1>>[F:23][C:24]1[CH:29]=[C:28]([OH:30])[C:27]([F:32])=[CH:26][C:25]=1[N:33]1[CH2:38][CH2:37][N:36]([S:39]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])(=[O:40])=[O:41])[CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 155270761-(4-Methoxyphenyl)-4-phenethylpiperazineHCID 231114774-(2,5-Difluoro-4-methoxyphenyl)-1-(octylsulfonyl)piperazine

Product 1

HCID 231114524-(2,5-Difluoro-4-hydroxyphenyl)-1-(octylsulfonyl)piperazineYield 87.4%

Procedure

Production Example 2 was repeated except that 1-(4-methoxyphenyl)-4-phenethylpiperazine was replaced with 4-(2,5-difluoro-4-methoxyphenyl)-1-(octylsulfonyl)piperazine (300 mg). The resulting crude product was purified on TLC (developer, hexane: ethyl acetate=11:5) to provide 4-(2,5-difluoro-4-hydroxyphenyl)-1-(octylsulfonyl)piperazine (253 mg).

Workup

  1. customThe resulting crude product was purified on TLC (developer, hexane: ethyl acetate=11:5)

Sources & evidence

ORD record
ord-6853523ae60544a68a174e3b0e35f827
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Reaction notes

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