2H-Azepine, 3,4,5,6-tetrahydro-7-methoxy- → 2-(alpha-Cyano-4-chlorobenzylidene)perhydroazepine

HRID 27426

Reaction equation

HRID 27426 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.CO[C:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]=1.N12CCCCC1C=CCCN2>CO>[C:7]([C:6](=[C:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19]1)[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1)#[N:8]

Participants

5

Reactant 3

HCID 756572H-Azepine, 3,4,5,6-tetrahydro-7-methoxy-HCID 2415824-Chlorobenzyl cyanideHCID 22258625Diazabicyclo[5.4.0]undec-5-ene

Product 1

HCID 705950422-(alpha-Cyano-4-chlorobenzylidene)perhydroazepineYield 67.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Agitate a mixture of 5.0 g of 4-chlorobenzyl cyanide, 5.5 g of caprolactim methyl ether and 0.5 g of diazabicyclo [5.4.0]undec-5-ene under nitrogen for 18 hours at 125°. Cool the thus-obtained reaction mixture to ambient temperature and then rub down the crystallizing residue with 20 ml of methyl alcohol before filtering to obtain 5.5 g of the title compound. Recrystallize this compound from methyl alcohol to obtain a product with a MP of 114° to 117°.

Workup

  1. temperatureCool
  2. customthe thus-obtained reaction mixture to ambient temperature
  3. filtrationbefore filtering

Sources & evidence

ORD record
ord-34ac4d4d324f4803aaa661b56366f157
Source dataset
uspto-grants-1980_09
Patent number
US04221788

Linked notes

Loading…