Dichloromethane → HCID 67917948, compound

HRID 1682012Notes

Reaction equation

HRID 1682012 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([CH2:8][N:9]2[C:15](=[O:16])[CH2:14][C:13]3[CH:17]=[C:18]([O:23][CH3:24])[C:19]([O:21][CH3:22])=[CH:20][C:12]=3[CH2:11][CH2:10]2)[CH2:2]1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH2:35][CH2:36]Br)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34].C(Cl)[Cl:39]>C(N(CC)CC)C.[OH-].[Na+]>[ClH:39].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH2:35][CH2:36][N:1]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([CH2:8][N:9]3[C:15](=[O:16])[CH2:14][C:13]4[CH:17]=[C:18]([O:23][CH3:24])[C:19]([O:21][CH3:22])=[CH:20][C:12]=4[CH2:11][CH2:10]3)[CH2:2]2)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 114706023,4-Dimethoxyphenethyl bromideHCID 198037373-[(hexahydro-azepin-3-yl)-methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Product 1

HCID 67917948HCID 67917948, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 14798Sodium HydroxideSolvent

Procedure

660 mg (2 mmol) of 3-[(hexahydro-azepin-3-yl)-methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one and 540 mg (2.2 mmol) of 2-(3,4-dimethoxyphenyl)-ethylbromide are refluxed for 1 hour in 3 ml of triethylamine. The reaction mixture is cooled and taken up in methylene chloride and 2-molar sodium hydroxide solution. The alkaline phase is separated off and extracted twice with methylene chloride. The combined organic phases are dried over magnesium sulphate and evaporated down in vacuo. Purification is carried out by column chromatography over 100 g of aluminium oxide (activity II, eluant: methylene chloride+0.3% ethanol). The fractions obtained are concentrated by evaporation in vacuo, the residue is dissolved in acetone and the hydrochloride is precipitated using ethereal hydrochloric acid.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customThe alkaline phase is separated off
  3. extractionextracted twice with methylene chloride
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. customevaporated down in vacuo
  6. customPurification
  7. customThe fractions obtained
  8. concentrationare concentrated by evaporation in vacuo
  9. dissolutionthe residue is dissolved in acetone
  10. customthe hydrochloride is precipitated

Sources & evidence

ORD record
ord-8b254e0fa187429bbc5b9ce8b6d1c3ab
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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