Hydrochloric Acid → alpha-(4-Fluorophenyl)-4-[(6-chloro-2-naphthyl)hydroxymethyl]-1-piperidinebutanol

HRID 1389883Notes

Reaction equation

HRID 1389883 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][C:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[O:24])[CH2:16][CH2:15]1)=[O:13])[CH:6]=[CH:5]2.[BH4-].[Na+].Cl.[OH-].[Na+]>C(O)C.O>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH:23]([OH:24])[CH2:22][CH2:21][CH2:20][N:17]2[CH2:16][CH2:15][CH:14]([CH:12]([C:7]3[CH:6]=[CH:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=4)[CH:8]=3)[OH:13])[CH2:19][CH2:18]2)=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 202956124-[4-(6-Chloro-2-naphthoyl)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone

Product 1

HCID 20295539alpha-(4-Fluorophenyl)-4-[(6-chloro-2-naphthyl)hydroxymethyl]-1-piperidinebutanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 4.4 g (0.01 mole) of 4-[4-(6-chloro-2-naphthoyl)-1-piperidyl]-1-(4-fluorophenyl)-1-butanone in 100 ml of absolute ethanol at 50° C. is gradually added 1.9 g (0.05 mole) sodium borohydride. Stirring is continued at 50° for one hour after the addition is completed and 20 ml of 3 N hydrochloric acid is added slowly. The mixture is diluted to 400 ml with water, made basic with sodium hydroxide, and extracted with chloroform. The organic phase is dried over MgSO4, concentrated in vacuo and recrystallized to yield α-(4-fluorophenyl)-4-[(6-chloro-2-naphthyl)hydroxymethyl]-1-piperidinebutanol.

Workup

  1. additionafter the addition
  2. extractionextracted with chloroform
  3. dry with materialThe organic phase is dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customrecrystallized

Sources & evidence

ORD record
ord-5f3ca6aefc354d0b90a3ec52bb2a1e3c
Source dataset
uspto-grants-1981_01
Patent number
US04246268

Reaction notes

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