1-Benzyl-4-piperidone → 1-Benzyl-4-(4-chloro-2-fluorobenzyl)-4-piperidinol

HRID 261491

Reaction equation

HRID 261491 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[C:4]([F:10])[CH:3]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([N:18]1[CH2:23][CH2:22][C:21]([CH2:6][C:5]2[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][C:4]=2[F:10])([OH:24])[CH2:20][CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 27365514-Chloro-2-fluorobenzyl bromide

Product 1

HCID 127332221-Benzyl-4-(4-chloro-2-fluorobenzyl)-4-piperidinol

Procedure

A sample of 4-chloro-2-fluorobenzyl bromide is converted to its Grignard reagent which is reacted with N-benzyl-4-piperidone to provide 1-benzyl-4-(4-chloro-2-fluorobenzyl)-4-piperidinol in the manner described in Example 4A. This product is distilled at 175°-180° C., 0.18 mm, to provide an orange oil which is converted in ether to its hydrogen chloride salt. The salt is recrystallized four times from an ethyl alcohol-ether mixture to provide the purified salt, mp 211.5°-213° C.

Sources & evidence

ORD record
ord-8bf40db80661482e915220dfee4b2b9e
Source dataset
uspto-grants-1979_08
Patent number
US04166119

Linked notes

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