Water → HCID 20498909, compound

HRID 128328Notes

Reaction equation

HRID 128328 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-a0bebb7249934569a09517660a949488
Source dataset
uspto-grants-1981_03
Patent number
US04259352

Reaction notes

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