Butyronitrile → HCID 178449874, compound

HRID 1492183Notes

Reaction equation

HRID 1492183 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:19])[CH2:16][CH2:17][CH3:18].[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24]>CO>[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24].[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:19])[CH2:16][CH2:17][CH3:18])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 8008ButyronitrileHCID 444972Fumaric AcidHCID 189522842-Morpholinoaniline hydrochloride

Product 1

HCID 178449874HCID 178449874, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 4-(2-aminophenyl)morpholine hydrochloride (7.5 g) and n-butyronitrile (20 ml) was heated at 170° C. in a sealed stainless steel pressure vessel for 60 hours. Excess n-butyronitrile was removed and the residue dissolved in water, basified with 10% aqueous sodium hydroxide solution to pH 12 and extracted with dichloromethane. The extract was washed with water and then brine, dried and the solvent removed. The residue was purified by chromatography on a neutral alumina column. Elution with a 1:1 mixture of dichloromethane and hexane removed unreacted starting material and then elution with a 1:99 mixture of methanol and dichloromethane yielded a solid which was dissolved in methanol (10 ml) and treated with fumaric acid (0.4 g) to give N-(2-morpholinophenyl)butyramidine monofumarate (m.p. 168°-170° C.) which was recrystallised from a 1:2 mixture of methanol and ether.

Workup

  1. customExcess n-butyronitrile was removed
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with water
  5. dry with materialbrine, dried
  6. customthe solvent removed
  7. customThe residue was purified by chromatography on a neutral alumina column
  8. washElution
  9. additionwith a 1:1 mixture of dichloromethane and hexane removed
  10. washelution
  11. additionwith a 1:99 mixture of methanol and dichloromethane
  12. customyielded a solid which

Sources & evidence

ORD record
ord-35f3add520c14fe7af7ddf0eff20f9d8
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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