Water → 1-Ethyl-2-(4-chlorobenzyl)perhydroazepine

HRID 27429Notes

Reaction equation

HRID 27429 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH3:23].O>C(C(C)=O)C>[CH2:22]([N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:7]1[CH2:6][C:5]1[CH:14]=[CH:15][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 39338092-[(4-Chlorophenyl)methyl]azepane

Product 1

HCID 233428031-Ethyl-2-(4-chlorobenzyl)perhydroazepine

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Boil together (under agitation) 4 g of 2-(4-chlorobenzyl)perhydroazepine, 2.5 g of anhydrous potassium carbonate and 2.9 g of ethyl bromide under reflux for 26 hours in 30 ml of ethylmethylketone. Cool the thus-produced reaction mixture to ambient temperature. Mix the cooled reaction mixture with water and then extract it with diethyl ether. Dry the resulting organic phase over sodium sulfate, remove the ether and distil the residue to obtain 5.12 g (70% of theory) of the title compound with a BP of 112° at 0.005 mm of Hg.

Workup

  1. temperatureCool
  2. customthe thus-produced reaction mixture to ambient temperature
  3. additionMix
  4. extractionextract it with diethyl ether
  5. dry with materialDry the resulting organic phase over sodium sulfate
  6. customremove the ether
  7. customdistil the residue

Sources & evidence

ORD record
ord-61b6237faed14f6ea997de5e8a8ecfe3
Source dataset
uspto-grants-1980_09
Patent number
US04221788

Reaction notes

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