N-4-Piperidylbenzamide → 4-Benzamido-1-(4-(indol-3-yl)-4-oxobutyl)piperidine
Reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:6].[C:16]([NH:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[C:16]([NH:24][CH:25]1[CH2:30][CH2:29][N:28]([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)=[O:6])[CH2:27][CH2:26]1)(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1Participants
Conditions
- Temperature
- 160 °C
Procedure
A mixture of 3-(4-chlorobutyryl)indole (22.2g. 0.1 mol.) and 4-benzamidopiperidine (40.8g. 0.2 mol.) was stirred and heated at 160° C. for 1 hour. The melt was cooled and extracted under reflux with water (200 ml.) for 0.5 hour. The insoluble granular residue was collected by filtration and crystallised from a mixture of ethanol (150 ml) and water (50 ml.), with charcoal treatment, to yield the title compound (15.5 g. 40%). The hydrochloride was precipitated from a solution of the base, in ethanol by addition of ethanolic hydrogen chloride (16.2 g. 38%) m.p. 275°-6° C. C24H27N3O. HCl 1/4 H2O requires C, 67.0 H, 6.7; N, 9.8 Found: C, 67.0; H, 6.7; N, 9.7%. It can also be precipitated from a solution of the base in dimethylformamide by addition of ethanolic hydrogen chloride and propan-2-ol. This gives the anhydrous form of the title compound hydrochloride m.p. 285.5° C.
Workup
- temperatureThe melt was cooled
- extractionextracted
- temperatureunder reflux with water (200 ml.) for 0.5 hour
- filtrationThe insoluble granular residue was collected by filtration
- customcrystallised from a mixture of ethanol (150 ml) and water (50 ml.), with charcoal treatment
Sources & evidence
- ORD record
- ord-7688624a2fbb4573abf7028243b6f300
- Source dataset
- uspto-grants-1977_07
- Patent number
- US04038401
Reaction notes
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