Propionyl chloride → HCID 12804763, compound

HRID 1106049Notes

Reaction equation

HRID 1106049 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][CH:19]=[CH:18][CH:17]=2)([OH:8])[CH2:4][CH2:3]1.[C:22]([Cl:26])(=[O:25])[CH2:23][CH3:24]>CCOCC>[ClH:26].[CH3:1][N:2]1[CH2:3][CH2:4][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][CH:19]=[CH:18][CH:17]=2)([O:8][C:22](=[O:25])[CH2:23][CH3:24])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 12542600HCID 12542600, compound

Product 1

HCID 12804763HCID 12804763, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.41 g of 1-methyl-4-(α-phenyl-2-tolyl)-4-piperidinol, Example 1, is treated with 5.0 ml of propionyl chloride with stirring and cooling. The reaction mixture, at ambient temperature, is stirred for 30 minutes and then permitted to stand for 137 hours under nitrogen. The mixture is diluted with 5.0 ml of ether, stirred for 5 minutes and the resulting precipitate collected by suction filtration. The filter cake is washed thoroughly with ether and recrystallized twice from isopropyl alcohol to give colorless crystals, mp 191°-193° C. of 1-methyl-4-(α-phenyl-2-tolyl)-4-propionyloxypiperidine hydrochloride.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture, at ambient temperature, is stirred for 30 minutes
  3. stirringstirred for 5 minutes
  4. filtrationthe resulting precipitate collected by suction filtration
  5. washThe filter cake is washed thoroughly with ether
  6. customrecrystallized twice from isopropyl alcohol

Sources & evidence

ORD record
ord-637119cea15d447fb53cf2b00d3ddb4d
Source dataset
uspto-grants-1982_01
Patent number
US04311703

Reaction notes

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