Sodium Chloride → 1-Acetyl-4-hydroxy-4-(1-methyl-2-propenyl)piperidine

HRID 982333Notes

Reaction equation

HRID 982333 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:11](Cl)[CH:12]=[CH:13][CH3:14].[Mg].[Cl-].[Na+]>CCOCC.O1CCCC1>[C:1]([N:4]1[CH2:9][CH2:8][C:7]([OH:10])([CH:13]([CH3:14])[CH:12]=[CH2:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 11589Crotyl chlorideHCID 122563N-Acetyl-4-piperidoneHCID 5462224Magnesium

Product 1

HCID 148520451-Acetyl-4-hydroxy-4-(1-methyl-2-propenyl)piperidine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.94 g 1-acetyl-4-piperidone in a mixture of ether (80 ml) and tetrahydrofuran (40 ml), was added dropwise at 10° C. or lower 275 ml of a 0.5M Grignard reagent prepared by the usual way from crotyl chloride and magnesium, and the resulting mixture was stirred overnight at room temperature. To the ice-cooled reaction mixture, was slowly added 100 ml of saturated aqueous solution of sodium chloride, and the layers were separated. The aqueous layer was extracted with chloroform, the two organic solutions were each concentrated, and the combined concentrate was subjected to silica gel column chromatography using, as eluent, a mixed solvent of ethyl acetate/n-hexane (1:1 by volume) containing 3% methanol, giving 16.9 g of 1-acetyl-4-hydroxy-4-(1-methyl-2-propenyl)piperidine as oil.

Workup

  1. additionwas added dropwise at 10° C.
  2. customreaction mixture
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with chloroform
  5. concentrationthe combined concentrate
  6. additiona mixed solvent of ethyl acetate/n-hexane (1:1 by volume) containing 3% methanol

Sources & evidence

ORD record
ord-67e8e135898142299a007b4679f912fc
Source dataset
uspto-grants-1991_02
Patent number
US04996210

Reaction notes

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