Allyl Alcohol → allyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate

HRID 35163Notes

Reaction equation

HRID 35163 reaction equation
[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([C:16]#[N:17])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C-]#N.[K+].[CH2:21]([OH:24])[CH:22]=[CH2:23]>>[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][N:7]([C:16](=[NH:17])[O:24][CH2:21][CH:22]=[CH2:23])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 7858Allyl AlcoholHCID 9032Potassium CyanideHCID 198338865,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile

Product 1

HCID 20041724allyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate

Procedure

A mixture of 1.99 g of 5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile, 0.59 g of potassium cyanide and 20 ml of allyl alcohol is stirred at room temperature for 20 hours and thereafter the allyl alcohol is distilled off. The residue is poured onto ice/water and extracted with methylene chloride, and the combined extracts are washed with water, dried over anhydrous sodium sulphate and evaporated. After flash chromatography on silica gel (elutent: ethyl acetate) there is obtained pure allyl 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboximidate as an oil.

Workup

  1. distillationthe allyl alcohol is distilled off
  2. additionThe residue is poured onto ice/water
  3. extractionextracted with methylene chloride
  4. washthe combined extracts are washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-bac92c456294430c80daef1d6f3fcce0
Source dataset
uspto-grants-1988_08
Patent number
US04766115

Reaction notes

Loading…