Acrylonitrile → HCID 14349028, compound

HRID 346063Notes

Reaction equation

HRID 346063 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]([F:28])([F:27])[C:9]1[CH:26]=[CH:25][C:12]([O:13][CH:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][NH:16][CH2:15]2)=[CH:11][CH:10]=1.[C:29](#[N:32])[CH:30]=[CH2:31]>C(O)(C)C>[C:29]([CH2:30][CH2:31][N:16]1[CH2:15][CH:14]([O:13][C:12]2[CH:25]=[CH:26][C:9]([C:8]([F:7])([F:27])[F:28])=[CH:10][CH:11]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17]1)#[N:32]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 14348987HCID 14348987, compound

Product 1

HCID 14349028HCID 14349028, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
95 °C

Procedure

A solution of 2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine of Example 1 (15 g, 0.049 mole) and acrylonitrile (5.2 g, 0.098 mole) in isopropanol (50 ml) was stirred at reflux (95° C.) for twenty hours. The reaction mixture was cooled then concentrated to an oil (17 g, 96%) of which 3.5 g was distilled to an oil of 3-(2-cyanoethyl)-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine (2.6 g, 235°-237° C./0.1 mm).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationthen concentrated to an oil (17 g, 96%) of which 3.5 g
  3. distillationwas distilled to an oil of 3-(2-cyanoethyl)-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine (2.6 g, 235°-237° C./0.1 mm)

Sources & evidence

ORD record
ord-fbc651f64cdd4d5d909fb2f73697dc6e
Source dataset
uspto-grants-1991_10
Patent number
US05059688

Reaction notes

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