1-Benzyl-4-piperidone → 1-Benzyl-4-(5-chloro-2-fluorobenzyl)-4-piperidinol

HRID 261473Notes

Reaction equation

HRID 261473 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH2:7]Br.[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]([CH2:7][C:6]2[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=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 27736262-(Bromomethyl)-4-chloro-1-fluorobenzene

Product 1

HCID 127332231-Benzyl-4-(5-chloro-2-fluorobenzyl)-4-piperidinol

Procedure

A sample of 5-chloro-2-fluorobenzyl bromide is converted to its Grignard reagent which is reacted with N-benzyl-4-piperidone to provide 1-benzyl-4-(5-chloro-2-fluorobenzyl)-4-piperidinol. The above is performed in a manner consistent with the procedure of Example 2A. This product is distilled at 210° C., 0.15 mm giving an orange oil. The oil is dissolved in ether where it is converted to its hydrochloride salt which is recrystallized thrice from an ethyl alcohol-ether mixture to provide the product, 1-benzyl-4-(5-chloro-2-fluorobenzyl)-4-piperidinol hydrochloride, mp 217°-219° C.

Sources & evidence

ORD record
ord-12f728548218494bb48e0731a3758bf2
Source dataset
uspto-grants-1979_08
Patent number
US04166120

Reaction notes

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