Valeronitrile → HCID 178446835, compound

HRID 1588596Notes

Reaction equation

HRID 1588596 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[C:15](#[N:20])[CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[Na+]>>[O:12]1[CH2:13][CH2:14][N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[NH:2][C:15](=[NH:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 8061ValeronitrileHCID 14798Sodium HydroxideHCID 189522842-Morpholinoaniline hydrochloride

Product 1

HCID 178446835HCID 178446835, compound

Procedure

A mixture of 4-(2-aminophenyl)morpholine hydrochloride (6.5 g) and valeronitrile (35 ml) were heated at 160°-165° C. under nitrogen for 25 hours and then cooled. The mixture was treated with aqueous sodium hydroxide and the basified mixture was extracted with dichloromethane. The solvent was removed by evaporation and the residue distilled under a pressure of 50 mm Hg to remove half the unreacted valeronitrile. A solid separated on cooling which was separated by filtration, washed with hexane (50 ml) and recrystallised from hexane to give N-(2-morpholinophenyl)valeramidine. (m.p. 135°-136° C.).

Workup

  1. temperaturewere heated at 160°-165° C. under nitrogen for 25 hours
  2. temperaturecooled
  3. extractionthe basified mixture was extracted with dichloromethane
  4. customThe solvent was removed by evaporation
  5. distillationthe residue distilled under a pressure of 50 mm Hg
  6. customto remove half the unreacted valeronitrile
  7. customA solid separated
  8. temperatureon cooling which
  9. customwas separated by filtration
  10. washwashed with hexane (50 ml)
  11. customrecrystallised from hexane

Sources & evidence

ORD record
ord-b3b44186c5f44f568033d91384857498
Source dataset
uspto-grants-1993_06
Patent number
US05223498

Reaction notes

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