Water → HCID 20498909, compound

HRID 2166774Notes

Reaction equation

HRID 2166774 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.I[CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[CH3:17].O>CN(C)P(N(C)C)(N(C)C)=O>[CH3:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[CH2:17][NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 133964-AminobenzonitrileHCID 13296846HCID 13296846, compound

Product 1

HCID 20498909HCID 20498909, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
120 °C

Procedure

4-Aminobenzonitrile (11.8 g.) and 1-iodomethyl-2-methylcyclopentane (16.3 g.) are dissolved in hexamethylphosphoramide (100 ml.) and heated under nitrogen in an oil bath maintained at 120° C. for 22 hours. The reaction mixture is cooled to room temperature and water (100 ml.) is added gradually. The mixture is then chilled in an ice bath. The precipitate separated is filtered, washed thoroughly with water, and dried. It is then washed repeatedly with hexane and dried. Recrystallization from ether-hexane affords 4-(2-methylcyclopentylmethylamino)benzonitrile as pale yellow crystals.

Workup

  1. temperatureheated under nitrogen in an oil bath
  2. temperatureThe reaction mixture is cooled to room temperature
  3. temperatureThe mixture is then chilled in an ice bath
  4. customThe precipitate separated
  5. filtrationis filtered
  6. washwashed thoroughly with water
  7. customdried
  8. washIt is then washed repeatedly with hexane
  9. customdried
  10. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-f8111a122af0406288d533d172b4dd2d
Source dataset
uspto-grants-1983_06
Patent number
US04388459

Reaction notes

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