Sodium Hydroxide → 1-[2-(3,4-Dimethoxyphenyl)ethyl]hexahydro-1H-azepine-2-ethanol

HRID 1682000Notes

Reaction equation

HRID 1682000 reaction equation
Cl.[OH:2][CH2:3][CH2:4][CH:5]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][NH:6]1.[OH-].[Na+].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH2:24][CH2:25]Br)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>C(Cl)Cl.C(N(CC)CC)C>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH2:24][CH2:25][N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:5]2[CH2:4][CH2:3][OH:2])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 114706023,4-Dimethoxyphenethyl bromideHCID 19803942109859-93-0

Product 1

HCID 198035011-[2-(3,4-Dimethoxyphenyl)ethyl]hexahydro-1H-azepine-2-ethanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

2.9 g (0.016 mol) of 2-(2-hydroxyethyl)-hexahydro-azepinehydrochloride are liberated with concentrated sodium hydroxide solution, taken up in methylene chloride and, after drying, evaporated down over magnesium sulphate. The residue is refluxed for 2 hours with 3.9 g (0.016 mol) of 2-(3,4-dimethoxy-phenyl)ethylbromide in 10 ml of triethylamine. After cooling, the reaction mixture is combined with 2 molar sodium hydroxide solution/methylene chloride. The alkaline phase is separated off and extracted twice with methylene chloride and the combined organic phases are dried over magnesium sulphate. The solvent is distilled off in vacuo and the residue is purified by column chromatography over aluminium oxide N (activity II, eluant: methylene chloride). Yield: 3.7 g (75.2% of theory).

Workup

  1. customafter drying
  2. customevaporated down over magnesium sulphate
  3. temperatureAfter cooling
  4. customThe alkaline phase is separated off
  5. extractionextracted twice with methylene chloride
  6. dry with materialthe combined organic phases are dried over magnesium sulphate
  7. distillationThe solvent is distilled off in vacuo
  8. customthe residue is purified by column chromatography over aluminium oxide N (activity II, eluant: methylene chloride)

Sources & evidence

ORD record
ord-13b7bceefe234f38b67554e0e4c2e1c6
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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