Ammonia → 4-(5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene)-1-(4-pyridinylcarbonyl)piperidine

HRID 275277

Reaction equation

P(Cl)(Cl)Cl.[N:5]1[CH:6]=[CH:7][N:8]2[CH2:14][CH2:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10](=[C:19]3[CH2:24][CH2:23][N+:22]([O-])([C:25]([C:27]4[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=4)=[O:26])[CH2:21][CH2:20]3)[C:9]=12.O.N>ClCCl>[N:5]1[CH:6]=[CH:7][N:8]2[CH2:14][CH2:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[C:10](=[C:19]3[CH2:24][CH2:23][N:22]([C:25]([C:27]4[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=4)=[O:26])[CH2:21][CH2:20]3)[C:9]=12

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of phosphorous trichloride (0.25 ml)in dichloromethane (3 ml) was added to a solution of 4-(5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene)-1-(4-pyridinylcarbonyl)-piperidine N1 -oxide (B, 0.4 g) and dichloromethane (5 ml). The reaction mixture was allowed to stir overnight at 25° C. in an atmosphere of nitrogen, and was then poured onto a mixture of ice and water. The resulting mixture was basified with concentrated aqueous ammonia, and the aqueous layer was extracted with dichloromethane. The dried (magnesium sulfate), filtered extracts were concentrated to give 4-(5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene )-1-(4-pyridinylcarbonyl)piperidine (A, 0.34 g), m.p. 207°-209° C. from carbon tetrachloride. ##STR25##

Workup

extractionthe aqueous layer was extracted with dichloromethane
dry with materialThe dried (magnesium sulfate)
filtrationfiltered extracts
concentrationwere concentrated

Sources & evidence

ORD record: ord-144e1a9cb859414384f4d4df3fd25ea8
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05393753

Linked notes

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