N-Phenethyl-4-piperidinone → 9-Phenethyl-1-phenyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole

HRID 647954Notes

Reaction equation

Cl.[NH:2]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]=2[CH:18]=1)N.[CH2:19]1[C:24](=O)[CH2:23][CH2:22][N:21]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:20]1>C(O)(C)C>[CH2:26]([N:21]1[CH2:22][CH2:23][C:24]2[NH:2][C:4]3[C:18]([C:19]=2[CH2:20]1)=[C:8]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][S:11][C:7]1=[CH:6][CH:5]=3)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 190 °C

Procedure

28.0 g of 5-hydrazino-3-phenylbenzothiophene hydrochloride are allowed to react with 21.0 g of N-(2-phenethyl)-4-piperidone in 500 ml of isopropanol at room temperature for 2 hours. After filtering off the crystall sludge, this is suspended in 150 ml of N NaOH and the suspension is extracted with methylene chloride. The organic phase is washed with water until neutral and evaporated, the oily residue is taken up in 400 ml of ethylene glycol and the mixture is heated to 190° C. for 30 minutes. The substance which has crystallised out after cooling is filtered off and recrystallised from toluene. Melting point: 220°-221° C.

Workup

filtrationAfter filtering off the crystall sludge
extractionthe suspension is extracted with methylene chloride
washThe organic phase is washed with water until neutral and
customevaporated
customThe substance which has crystallised out
temperatureafter cooling
filtrationis filtered off
customrecrystallised from toluene

Sources & evidence

ORD record: ord-435995b547684be592cbb36143f2d1d8
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04410536

Reaction notes

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