Benzoyl chloride → HCID 12804767, compound

HRID 1733324Notes

Reaction equation

HRID 1733324 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[F:23])([OH:8])[CH2:4][CH2:3]1.[C:24]([Cl:32])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CCOCC>[ClH:32].[C:24]([O:8][C:5]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[F:23])[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 12804754HCID 12804754, compound

Product 1

HCID 12804767HCID 12804767, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.5 g of 1-methyl-4[α-(2-fluoro-4-methylphenyl)-2-tolyl]-4-piperidinol, Example 4, is treated carefully with 7 ml of benzoyl chloride with stirring and cooling. The reaction mixture is stirred for 16 hours at ambient temperature and then diluted with 15 ml of ether. The resulting precipitate is filtered, washed with ether, converted to the free base which is column chromatographed on an alumina column using ether as the eluant. The free base is converted to its hydrogen chloride salt which is recrystallized from a methanol-acetone-ether mixture to give a white powder, mp 218°-219° C. of 4-benzoyloxy-4-[α-(2-fluoro-4-methylphenyl)-2-tolyl]-1-methylpiperidine hydrochloride.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture is stirred for 16 hours at ambient temperature
  3. filtrationThe resulting precipitate is filtered
  4. washwashed with ether
  5. customchromatographed on an alumina column
  6. customis recrystallized from a methanol-acetone-ether mixture

Sources & evidence

ORD record
ord-402ca8d5d32840ffaedbf7e0e75de002
Source dataset
uspto-grants-1980_12
Patent number
US04241071

Reaction notes

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