Hydrochloric Acid → 4-[4-[(4-Chlorophenyl)hydroxymethyl]-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone

HRID 866868Notes

Reaction equation

HRID 866868 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH:21]([C:24](=[O:32])[C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[CH2:20][CH2:19]3)OCC[O:11]2)=[CH:6][CH:5]=1.C(O)C.Cl>O.[OH-].[Na+]>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH:24]([CH:21]2[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH2:15][C:10](=[O:11])[C:7]3[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=3)[CH2:19][CH2:20]2)[OH:32])=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 20318878HCID 20318878, compound

Product 1

HCID 114747524-[4-[(4-Chlorophenyl)hydroxymethyl]-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Sodium borohydride (0.4 g., 0.01 mole) was added in small portions to a stirring solution of 2.2 g. (0.0052 mole) of 2-(p-fluorophenyl)-2-{3-[4-(p-chlorobenzoyl)piperidino]propyl}-1,3-dioxolane in 20 ml. of absolute ethanol. The reaction mixture was stirred until gas evolution ceased and then dilute hydrochloric acid was added dropwise until an acidic solution was obtained. After stirring overnight the mixture was diluted with water and basified with dilute sodium hydroxide. The free base was extracted into chloroform, the chloroform solution was washed with water, dried over magnesium sulfate, filtered, and the filtrate concentrated under vacuum. The residual oil crystallized on trituration with isopropyl ether to give 1.2 g. (60%) of a light brown solid which melted at 143°-146° C. Recrystallization of the solid from benzene-isooctane gave 0.8 g. of a white powdery solid which melted at 146.5°-147° C.

Workup

  1. customwas obtained
  2. stirringAfter stirring overnight the mixture
  3. extractionThe free base was extracted into chloroform
  4. washthe chloroform solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe residual oil crystallized on trituration with isopropyl ether
  9. customto give 1.2 g
  10. customRecrystallization of the solid from benzene-isooctane
  11. customgave 0.8 g

Sources & evidence

ORD record
ord-f96c1814ecd54507b6ba3a91f441e32b
Source dataset
uspto-grants-1978_07
Patent number
US04101662

Reaction notes

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