2H-Azepine, 3,4,5,6-tetrahydro-7-methoxy- → N-[(1R,2R)-2-phenylcyclopentyl]azepan-2-imine;hydrochloride

HRID 461034Notes

Reaction equation

HRID 461034 reaction equation
[ClH:1].[C:2]1([C@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[NH2:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]=1>C(O)C>[ClH:1].[C:2]1([C@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[N:13]=[C:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 756572H-Azepine, 3,4,5,6-tetrahydro-7-methoxy-HCID 70051154rac-(1R,2R)-2-phenylcyclopentan-1-amine hydrochloride

Product 1

HCID 145795653N-[(1R,2R)-2-phenylcyclopentyl]azepan-2-imine;hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolCatalyst

Procedure

A mixture of 4.0 g of cis-2-phenylcyclopentylamine hydrochloride, M.P. 205°-206° C and 5.0 ml of O-methylcaprolactim is allowed to stand at room temperature for 6 days with occasional stirring. A few drops of ethanol are added to maintain a stirrable slurry, after which the mixture is cooled. The resulting solid is washed with ether and recrystallized from acetone/methanol to give the desired product, M.P. 181.5°-183.5° C (dec.).

Workup

  1. temperatureto maintain a stirrable slurry
  2. temperatureafter which the mixture is cooled
  3. washThe resulting solid is washed with ether
  4. customrecrystallized from acetone/methanol

Sources & evidence

ORD record
ord-9dcbb9a606b14c8c9b3bed0db9e363fa
Source dataset
uspto-grants-1977_12
Patent number
US04061746

Reaction notes

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