4-Methylbenzoyl Chloride → 2'-[2-(1-Methyl-2-piperidyl)ethyl]-p-toluanilide

HRID 1579352Notes

Reaction equation

HRID 1579352 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[CH3:12].[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:23](Cl)=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH3:12][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[CH2:5][CH2:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[NH:1][C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:26])=[CH:18][CH:19]=1)=[O:24]

Participants

4

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 110852822-(2-Aminophenethyl)-1-methylpiperidine

Product 1

HCID 205600772'-[2-(1-Methyl-2-piperidyl)ethyl]-p-toluanilide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Reaction of 2-(o-aminophenethyl)-1-methylpiperidine (80 g., 0.036 mole) with p-toluoyl chloride (6.2 g., 0.04 mole) in 50 ml. of pyridine according to the method of Example 25 provides 2'-[2-(1-methyl-2-piperidyl)ethyl]-p-toluanilide. Crystallization from isopropyl ether and then from isopropyl alcohol provides 3.9 g., (32%) of analytically pure material, m.p. 90.5- 92°C. (corr.).

Sources & evidence

ORD record
ord-069d31b07a0e44da81cbe2e7b09740d2
Source dataset
uspto-grants-1976_01
Patent number
US03931195

Reaction notes

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