1-(4-Benzyloxy-3-chlorophenyl)-4-(3-cyclohexylpropyl)piperazine → 2-Fluoro-4-[4-(3-phenylpropyl)piperazin-1-yl]phenol

HRID 269901

Reaction equation

HRID 269901 reaction equation
C(OC1C=CC(N2CCN(CCCC3CCCCC3)CC2)=CC=1Cl)C1C=CC=CC=1.C([O:38][C:39]1[CH:44]=[CH:43][C:42]([N:45]2[CH2:50][CH2:49][N:48]([CH2:51][CH2:52][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH2:47][CH2:46]2)=[CH:41][C:40]=1[F:60])C1C=CC=CC=1>>[F:60][C:40]1[CH:41]=[C:42]([N:45]2[CH2:46][CH2:47][N:48]([CH2:51][CH2:52][CH2:53][C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=3)[CH2:49][CH2:50]2)[CH:43]=[CH:44][C:39]=1[OH:38]

Participants

3

Reactant 2

HCID 231114081-(4-Benzyloxy-3-chlorophenyl)-4-(3-cyclohexylpropyl)piperazineHCID 231114371-(4-Benzyloxy-3-fluorophenyl)-4-(3-phenylpropyl)-piperazine

Product 1

HCID 231114062-Fluoro-4-[4-(3-phenylpropyl)piperazin-1-yl]phenolYield 73.1%

Procedure

Production Example 30 was repeated except that 1-(4-benzyloxy-3-chlorophenyl)-4-(3-cyclohexylpropyl)piperazine was replaced with 1-(4-benzyloxy-3-fluorophenyl)-4-(3-phenylpropyl)-piperazine (394 mg). The resulting crude product was purified on TLC (developer, chloroform: methanol=10:1) to provide 2-fluoro-4-[4-(3-phenylpropyl)piperazin-1-yl]phenol (224 mg).

Workup

  1. customThe resulting crude product was purified on TLC (developer, chloroform: methanol=10:1)

Sources & evidence

ORD record
ord-afb87b17d5614531bf0bf79ebf153926
Source dataset
uspto-grants-2008_11
Patent number
US07449466B2

Linked notes

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