1-(4-Methoxyphenyl)-4-phenethylpiperazine → 4-(4-Benzylpiperidino)-2,5-difluorophenol

HRID 269910Notes

Reaction equation

HRID 269910 reaction equation
COC1C=CC(N2CCN(CCC3C=CC=CC=3)CC2)=CC=1.[CH2:23]([CH:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:41]=[C:40]([F:42])[C:39]([O:43]C)=[CH:38][C:37]=2[F:45])[CH2:32][CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([CH:30]1[CH2:31][CH2:32][N:33]([C:36]2[C:37]([F:45])=[CH:38][C:39]([OH:43])=[C:40]([F:42])[CH:41]=2)[CH2:34][CH2:35]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 155270761-(4-Methoxyphenyl)-4-phenethylpiperazineHCID 231114884-Benzyl-1-(2,5-difluoro-4-methoxyphenyl)piperidine

Product 1

HCID 231114804-(4-Benzylpiperidino)-2,5-difluorophenolYield 48.1%

Procedure

Production Example 2 was repeated except that 1-(4-methoxyphenyl)-4-phenethylpiperazine was replaced with 4-benzyl-1-(2,5-difluoro-4-methoxyphenyl)piperidine (300 mg). The resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=4:1) to provide 4-(4-benzylpiperidino)-2,5-difluorophenol (138 mg).

Workup

  1. customThe resulting crude product was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1b615a287fed4b68a80a9d1bf49b6e3c
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Reaction notes

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