1-(2,5-Difluoro-4-methoxyphenyl)-4-(3-phenylpropyl)piperidine → 2,5-Difluoro-4-[4-(3-phenylpropyl)piperidino]phenol

HRID 269914Notes

Reaction equation

HRID 269914 reaction equation
COC1C=CC(N2CCN(CCC3C=CC=CC=3)CC2)=CC=1C.[F:24][C:25]1[CH:30]=[C:29]([O:31]C)[C:28]([F:33])=[CH:27][C:26]=1[N:34]1[CH2:39][CH2:38][CH:37]([CH2:40][CH2:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:36][CH2:35]1>>[F:33][C:28]1[CH:27]=[C:26]([N:34]2[CH2:39][CH2:38][CH:37]([CH2:40][CH2:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:36][CH2:35]2)[C:25]([F:24])=[CH:30][C:29]=1[OH:31]

Participants

3

Reactant 2

HCID 231115061-(2,5-Difluoro-4-methoxyphenyl)-4-(3-phenylpropyl)piperidineHCID 231115101-(4-Methoxy-3-methylphenyl)-4-phenethylpiperazine

Product 1

HCID 231113942,5-Difluoro-4-[4-(3-phenylpropyl)piperidino]phenolYield 32.2%

Procedure

Production Example 10 was repeated except that 1-(4-methoxy-3-methylphenyl)-4-phenethylpiperazine was replaced with 1-(2,5-difluoro-4-methoxyphenyl)-4-(3-phenylpropyl)piperidine (230 mg). The resulting crude product was purified on TLC (developer, hexane: ethyl acetate=3:1) to provide 2,5-difluoro-4-[4-(3-phenylpropyl)piperidino]phenol (71 mg).

Workup

  1. customThe resulting crude product was purified on TLC (developer, hexane: ethyl acetate=3:1)

Sources & evidence

ORD record
ord-5afcd5f2d0294d22af442930a2be759c
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Reaction notes

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