7-dimethylamino-9-phenyl-6,7-dihydro [5H] benzocycloheptene → 7-dimethylamino-5-phenyl-6,7,8,9-tetrahydro [5H] benzocycloheptene

HRID 372545Notes

Reaction equation

[CH3:1][N:2]([CH3:20])[CH:3]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=2[CH2:5][CH2:4]1>C(O)C>[CH3:1][N:2]([CH3:20])[CH:3]1[CH2:4][CH2:5][C:6]2[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=2[CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9]1

Participants

Conditions

Temperature: 20 °C

Procedure

5 g of palladized carbon [10% Pd(OH)2 ] were added to a solution of 5 g of 7-dimethylamino-9-phenyl-6,7-dihydro [5H] benzocycloheptene in 250 ml of ethanol and the mixture was stirred under a hydrogen atmosphere at 20° C until absorption ceased. The mixture was filtered and the filtrate was evaporated to dryness. The residue was chromatographed over silica gel and elution with a 9-1-1 cyclohexane-ethyl acetate-triethylamine mixture yielded 0.52 g of isomer A (equatorial 5-H) and 2.9 g of isomer B (axial 5-H) of 7-dimethylamino-5-phenyl-6,7,8,9-tetrahydro [5H] benzocycloheptene.

Workup

filtrationThe mixture was filtered
customthe filtrate was evaporated to dryness
customThe residue was chromatographed over silica gel and elution with a 9-1-1 cyclohexane-ethyl acetate-triethylamine mixture

Sources & evidence

ORD record: ord-b6f01544bc8e48688180f3ab44a49dd8
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04091115

Reaction notes

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