Chloroform → 5,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile

HRID 35174

Reaction equation

HRID 35174 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]([NH2:18])=O)[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[OH-].[Na+]>C(N(CC)CC)C>[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:18])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 200417145,7-dihydro-6H-dibenz[c,e]azepine-6-carboxamide

Product 1

HCID 198338865,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 1.19 g of 5,7-dihydro-6H-dibenz[c,e]azepine-6-carboxamide (see Example 10), 12 ml of chloroform, 2.7 ml of 50% sodium hydroxide solution and 50 mg of triethylamine is stirred at room temperature for 1 hour. The reaction mixture is then poured onto ice/water and the whole is extracted with methylene chloride. The extracts are washed with water, dried over anhydrous sodium sulphate and evaporated, and the residue is purified by flash chromatography on silica gel [eluent: n-hexane/ethyl acetate (9:1)]. There is obtained 5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile, m.p. 118°-121° C.

Workup

  1. additionThe reaction mixture is then poured onto ice/water
  2. extractionthe whole is extracted with methylene chloride
  3. washThe extracts are washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated
  6. customthe residue is purified by flash chromatography on silica gel [eluent: n-hexane/ethyl acetate (9:1)]

Sources & evidence

ORD record
ord-a3652c614646498fbe2e542a6a54e1ec
Source dataset
uspto-grants-1988_08
Patent number
US04766115

Linked notes

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