Dimethylcyanamide → 1,1-Dimethyl-2-(2-morpholinophenyl)guanidine

HRID 1588681Notes

Reaction equation

HRID 1588681 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.[CH3:15][N:16]([CH3:19])[C:17]#[N:18]>>[CH3:15][N:16]([CH3:19])[C:17]([NH2:18])=[N: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

Participants

3

Reactant 2

HCID 15112DimethylcyanamideHCID 189522842-Morpholinoaniline hydrochloride

Product 1

HCID 98854071,1-Dimethyl-2-(2-morpholinophenyl)guanidine

Conditions

Temperature
10 °C

Procedure

A mixture of 4-(2-aminophenyl)morpholine hydrochloride (2.1 g) and N,N-dimethylcyanamide (7 ml) was heated under nitrogen at 165°-170° C. for 12 hours. The reaction mixture was cooled to 10° C. and the precipitate collected by filtration, washed with ether and stirred with 40% aqueous sodium hydroxide solution. The resulting mixture was extracted with dichloromethane and the extract washed with brine and dried. Removal of the solvent yielded a residue which was recrystallised from hexane to give 1,1-dimethyl-2-(2-morpholinophenyl)guanidine (m.p. 144°-145° C.).

Workup

  1. temperaturewas heated under nitrogen at 165°-170° C. for 12 hours
  2. filtrationthe precipitate collected by filtration
  3. washwashed with ether
  4. extractionThe resulting mixture was extracted with dichloromethane
  5. washthe extract washed with brine
  6. customdried
  7. customRemoval of the solvent
  8. customyielded a residue which
  9. customwas recrystallised from hexane

Sources & evidence

ORD record
ord-d43df0c4cefa47d48c41804543a7cb6e
Source dataset
uspto-grants-1993_06
Patent number
US05223498

Reaction notes

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