Water → HCID 19803812, compound

HRID 1682001Notes

Reaction equation

HRID 1682001 reaction equation
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:15][CH2:16][N:17]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:18]2[CH2:24][CH2:25]O)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].O.[OH-].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:2][CH2:25][CH2:24][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:17]1[CH2:16][CH2:15][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 198035011-[2-(3,4-Dimethoxyphenyl)ethyl]hexahydro-1H-azepine-2-ethanol

Product 1

HCID 19803812HCID 19803812, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4 ml of phosphorus tribromide are added dropwize to 2.9 g (9.4 mmol) of N-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-(2-hydroxyethyl)-hexahydro-azepine in 100 ml of carbon tetrachloride, whilst cooling with ice, and the mixture is stirred for 15 hours at ambient temperature. Then water is added, whilst cooling with ice water is continued, and the mixture is made slightly alkaline with 2 molar sodium hydroxide solution. The aqueous/alkaline solution is separated off and extracted twice with methylene chloride. The combined organic solutions are dried over magnesium sulphate and concentrated by evaporation in vacuo. Yield: 3.6 g (100% of theory).

Workup

  1. temperaturewhilst cooling with ice
  2. customThe aqueous/alkaline solution is separated off
  3. extractionextracted twice with methylene chloride
  4. dry with materialThe combined organic solutions are dried over magnesium sulphate
  5. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-5e44c1e6f9fa465fa238559248fe86e8
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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