HCID 13691017, compound → HCID 13691027, compound

HRID 622137Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

2-(4-Benzyl-1-piperazinyl)-4-phenyl-1-azaspiro[4.5]deca-1,3,6,9-tetraen-8-one (14.6 g) is heated for 10 minutes to a temperature of about 200° C. After being cooled to a temperature of about 20° C., the residue obtained is dissolved in methylene chloride (500 cc) and the solution is poured into silica (300 g) contained in a column 4.2 cm in diameter. Elution is performed first with pure methylene chloride (4 liters); the corresponding eluate is rejected. Elution is then performed with a mixture of methylene chloride and methanol (90:10 by volume) (3 liters) and the eluate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. After recrystallization of the residue in acetonitrile (200 cc), 3-(4-benzyl-1-piperazinyl)-1-phenyl-7H-pyrrolo[1,2-a]azepin-7-one (10.5 g), m.p. 157° C., is obtained.

Workup

customthe residue obtained
additionthe solution is poured into silica (300 g)
washElution
washElution
additionis then performed with a mixture of methylene chloride and methanol (90:10 by volume) (3 liters)
customthe eluate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
customAfter recrystallization of the residue in acetonitrile (200 cc)

Sources & evidence

ORD record: ord-89491ebec93b4959adf012a6d80f820c
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04769366

Reaction notes

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