Propionyl chloride → N-acetyl-4-(4-n-propylphenyl)-piperidine

HRID 1448978Notes

Reaction equation

C(N1CCC(C2C=CC=CC=2)CC1)(=O)C.C(Cl)(=O)CC.[Cl-].[Cl-].[Cl-].[Al+3].[C:25]([N:28]1[CH2:33][CH2:32][CH:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40](=O)[CH2:41][CH3:42])=[CH:36][CH:35]=2)[CH2:30][CH2:29]1)(=[O:27])[CH3:26]>>[C:25]([N:28]1[CH2:33][CH2:32][CH:31]([C:34]2[CH:35]=[CH:36][C:37]([CH2:40][CH2:41][CH3:42])=[CH:38][CH:39]=2)[CH2:30][CH2:29]1)(=[O:27])[CH3:26]

Participants

Reactant 4

HCID 62324Propionyl chloride

HCID 6451240Aluminum(III) Chloride

HCID 11608128HCID 11608128, compound

HCID 13151836N-acetyl-4-(4-propionylphenyl)-piperidine

Product 1

HCID 13151837N-acetyl-4-(4-n-propylphenyl)-piperidine

Procedure

The starting material can be produced, for example, by reaction of 18 g of N-acetyl-4-phenyl-piperidine and 11.5 g of propionic acid chloride, in the presence of aluminium trichloride, to N-acetyl-4-(4-propionylphenyl)-piperidine and then catalytic hydrogenation thereof to give N-acetyl-4-(4-n-propylphenyl)-piperidine, b.p.0.03 =160°.

Sources & evidence

ORD record: ord-5d1e1cc345d741418c17f87d6815b6f2
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04188396

Reaction notes

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