Benzene → 1-methyl-4-(9-cyano-11H-pyrrolo[2,1-b][3]benzazepin-11-ylidene)piperidine

HRID 1701711Notes

Reaction equation

HRID 1701711 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16](Br)[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][N:10]3[CH:20]=[CH:21][CH:22]=[C:9]23)[CH2:4][CH2:3]1.C1C=CC=CC=1.[C-:29]#[N:30].[Na+].O>CN(C)C=O>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([C:29]#[N:30])[CH:17]=[CH:18][C:13]=3[CH:12]=[CH:11][N:10]3[CH:20]=[CH:21][CH:22]=[C:9]23)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 241Benzene2×HCID 962WaterHCID 8929Sodium CyanideHCID 131411821-Methyl-4-[9-bromo-11H-pyrrolo[2,1-b] [3]benzazepin-11-ylidene]piperidine

Product 1

HCID 129093871-methyl-4-(9-cyano-11H-pyrrolo[2,1-b][3]benzazepin-11-ylidene)piperidineYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Methyl-4-(9-bromo-11H-pyrrolo[2,1-b][3]benzazepin-11-ylidene)piperidine (6.3 g, 0.019 mole) and cuprous cyanide (3.2 g, 0.035 mole) in 25 ml of dry dimethylformamide are refluxed under nitrogen for five hours. The mixture is cooled to an internal temperature of 50° and treated with 60 ml each of benzene and aqueous saturated sodium cyanide solution. After stirring one hour the contents are transferred to a separatory funnel with the aid of additional benzene and water. The aqueous phase is extracted two times with benzene, once with ether and the combined benzene-ether extracts are washed successively with dilute sodium cyanide, water, dilute ammonium hydroxide, and water. Upon drying over sodium sulfate the solvents are evaporated in vacuo to give 1-methyl-4-(9-cyano-11H-pyrrolo[2,1-b][3]benzazepin-11-ylidene)piperidine as an oil (5.0 g, 87%). Trituration with acetonitrile gives a solid (3.6 g, m.p. 156°-159°). An analytical sample is obtained after one recystallization from acetonitrile, m.p. 158°-161°.

Workup

  1. temperatureThe mixture is cooled to an internal temperature of 50°
  2. extractionThe aqueous phase is extracted two times with benzene
  3. washonce with ether and the combined benzene-ether extracts are washed successively with dilute sodium cyanide, water, dilute ammonium hydroxide, and water
  4. dry with materialUpon drying over sodium sulfate the solvents
  5. customare evaporated in vacuo

Sources & evidence

ORD record
ord-20da9f7920a247e6a02a9dc86a48ca57
Source dataset
uspto-grants-1980_03
Patent number
US04195091

Reaction notes

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