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

HRID 372546Notes

Reaction equation

C(O)C.[CH3:4][N:5]([CH3:24])[CH:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[C:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(O)[CH2:7]1.N.[Na]>O1CCCC1>[CH3:4][N:5]([CH3:24])[CH:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[CH:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:7]1

Participants

Conditions

Temperature: -40 °C

Procedure

12.4 ml of ethanol and then a solution of 12 g of 7-dimethylamino-5ξ-phenyl-5ξ-hydroxy-6,7,8,9-tetrahydro [5H] benzocycloheptene in 200 ml of tetrahydrofuran were added to 600 ml of condensed ammonia and then 2.46 of sodium were added at -40° C. The mixture was stirred at -40° C for 20 minutes and the ammonia and tetrahydrofuran were evaporated. The residue was dissolved in ethyl acetate and the solution was washed with water, dried and evaporated to dryness. The residue was chromatographed over silica gel and eluted with a 9-1-1 cyclohexane-ethyl acetate-triethylamine mixture to obtain 3.2 g of isomer A (equatorial 5-H) and 6.5 g of isomer B (axial 5-H) of 7-dimethylamino-5-phenyl-6,7,8,9-tetrahydro [5H] benzocycloheptene.

Workup

customthe ammonia and tetrahydrofuran were evaporated
dissolutionThe residue was dissolved in ethyl acetate
washthe solution was washed with water
customdried
customevaporated to dryness
customThe residue was chromatographed over silica gel
washeluted with a 9-1-1 cyclohexane-ethyl acetate-triethylamine mixture

Sources & evidence

ORD record: ord-a3cdf67ac2a14469abac105df2e3daf2
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04091115

Reaction notes

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