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

HRID 372543Notes

Reaction equation

HRID 372543 reaction equation
[CH3:1][N:2]([CH3:15])[CH:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[C:5](=[O:14])[CH2:4]1.[C:16]1([Li])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+].O>C(OCC)C>[CH3:1][N:2]([CH3:15])[CH:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:14])[CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 544675237-dimethylamino-5-oxo-6,7,8,9-tetrahydro [5H] benzocyclohepteneHCID 178506676HCID 178506676, compound

Product 1

HCID 542538337-dimethylamino-5-phenyl-5-hydroxy-6,7,8,9-tetrahydro [5H] benzocycloheptene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 24.46 g of 7-dimethylamino-5-oxo-6,7,8,9-tetrahydro [5H] benzocycloheptene in 488 ml of ethyl ether was added over 75 minutes under a nitrogen atmosphee at 0° to 5° C to a solution of 1.2 M of phenyl lithium in ethyl ether and the mixture was stirred for 2 hours at 0° to 5° C. 120 ml of an aqueous saturated ammonium chloride solution and then 100 ml of water were slowly added thereto at 0° to 15° C and the mixture was decanted. The ether phase was washed with water and dried to obtain 29.4 g of raw 7-dimethylamino-5ξ-phenyl-5ξ-hydroxy6,7,8,9-tetrahydro [5H] benzocycloheptene which was used as is for the next step. The product was a mixture of the 2 isomers with substitution in the 5-position.

Workup

  1. customat 0° to 15° C and the mixture was decanted
  2. washThe ether phase was washed with water
  3. customdried

Sources & evidence

ORD record
ord-ebb885159d3c4bc38081b79e25cdaf50
Source dataset
uspto-grants-1978_05
Patent number
US04091115

Reaction notes

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