Butyronitrile → HCID 178449873, compound

HRID 1492184Notes

Reaction equation

HRID 1492184 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[C:18](#[N:22])[CH2:19][CH2:20][CH3:21].[OH-].[Na+]>>[O:15]1[CH2:16][CH2:17][N:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:18](=[NH:22])[CH2:19][CH2:20][CH3:21])[CH2:13][CH2:14]1

Participants

5

Reactant 4

HCID 8008ButyronitrileHCID 14798Sodium HydroxideHCID 7357562-MorpholinoanilineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178449873HCID 178449873, compound

Procedure

Powdered anhydrous aluminium chloride (12 g) was added portion-wise to a stirred slurry of 4-(2-aminophenyl)morpholine (5.34 g) and n-butyronitrile (6 g) at 40°-50° C. The mixture was then heated at 160°-170° C. for 6 hours, allowed to cool and then digested with 40% aqueous sodium hydroxide solution. The solution was extracted with ether and the extract washed with water and brine and dried. Removal of the solvent gave a residue which was crystallised from a 1:1 mixture of ethylacetate and hexane to give N-(2-morpholinophenyl)butyramidine (m.p. 131°) which was converted into its monofumarate salt (m.p. 173° C.) which was recrystallised from propan-2-ol.

Workup

  1. temperatureThe mixture was then heated at 160°-170° C. for 6 hours
  2. temperatureto cool
  3. extractionThe solution was extracted with ether
  4. washthe extract washed with water and brine
  5. customdried
  6. customRemoval of the solvent
  7. customgave a residue which
  8. customwas crystallised from a 1:1 mixture of ethylacetate and hexane

Sources & evidence

ORD record
ord-7857051fe4ed45559100d70f8363f580
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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