8-Methoxy-2,3,4,5,6,7-hexahydroazocine → 3-(1-Phenylcyclohexyl)-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine

HRID 349171Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]([NH:16][NH2:17])=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CO[C:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]=1>C1(C)C=CC=CC=1>[C:5]1([C:8]2([C:14]3[N:27]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]4=[N:17][N:16]=3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Anhydrous toluene was added to a mixture of 1-(4-chlorophenyl)cyclohexanecarbohydrazide (62 mg) and 8-methoxy-2,3,4,5,6,7-hexahydroazocine (40.1 mg). The reaction vessel was heated to 120° C. overnight, whereupon it was cooled to room temperature and the solvent was evaporated. The crude product was purified by column chromatography to give 3-(1-phenylcyclohexyl)-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (2-51) as a white solid.

Workup

temperaturewas cooled to room temperature
customthe solvent was evaporated
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-0a6203393ecf44328cf6c6169672773a
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179802B2

Reaction notes

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