Hydrochloric Acid → HCID 20368928, compound

HRID 1576118Notes

Reaction equation

HRID 1576118 reaction equation
[OH:1][C:2]1([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[CH2:7][CH2:6][N:5]([CH:8]([F:27])[CH2:9][CH:10]([NH:19]CC2C=CC=CC=2)[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH2:4][CH2:3]1.[ClH:38]>[Pd].C(O)C.[H][H]>[ClH:38].[OH:1][C:2]1([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:35])[F:36])[CH:29]=2)[CH2:7][CH2:6][N:5]([CH:8]([F:27])[CH2:9][CH:10]([NH2:19])[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:12])[CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 21514098HCID 21514098, compound

Product 1

HCID 20368928HCID 20368928, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent2×

Procedure

A mixture of γ-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidin-1-yl]-2-benzylamino-4-fluorobutyrophenone (3.8 g), 10 % palladium on charcoal (1.0 g) and 35 % hydrochloric acid (2.0 g) in ethanol (45 ml) was vigorously stirred in hydrogen atmosphere at 25°C until an equimolar amount of hydrogen was consumed. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to afford γ-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidin-1-yl]-2-amino-4-fluorobutyrophenon hydrochloride. M.P. 230° - 235°C (decomposition). The hydrochloride was shaken with a mixture of aqueous ammonia and ether. The ethereal layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield the free base, which was recyrstallized from aqueous ethanol. M.P. 105° - 107°C.

Workup

  1. customwas consumed
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8266142e43ee4f02b3678f215e668038
Source dataset
uspto-grants-1976_09
Patent number
US03979390

Reaction notes

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