M-Cresol → HCID 18952265, compound

HRID 1492294Notes

Reaction equation

HRID 1492294 reaction equation
Cl.[CH2:2]([C:6]1[CH:7]=[CH:8][C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[C:10]([CH:12]=1)[NH2:11])[CH:3]([CH3:5])[CH3:4].[CH3:19][N:20]([CH3:23])[C:21]#[N:22].C1C(O)=CC=CC=1C>>[CH3:19][N:20]([CH3:23])[C:21]([NH2:22])=[N:11][C:10]1[CH:12]=[C:6]([CH2:2][CH:3]([CH3:5])[CH3:4])[CH:7]=[CH:8][C:9]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

4

Reactant 3

HCID 342M-CresolHCID 15112DimethylcyanamideHCID 18952282HCID 18952282, compound

Product 1

HCID 18952265HCID 18952265, compound

Procedure

A mixture of 5-isobutyl-2-morpholinoaniline hydrochloride (4.1 g), N,N-dimethylcyanamide (1.77 g) and m-cresol (15 ml) was heated at 90°-95° C. for 6 hours to yield a residue which was extracted with hot hexane, decolourised with charcoal and purified by chromatography on an alumina column eluted with a 2:98 mixture of methanol and dichloromethane. The resulting product was crystallised from a 1:3 mixture of ethylacetate and hexane. The initial precipitate was removed by filtration and the filtrate evaporated to dryness to give a residue which was recrystallised from a 1:3 mixture of ethylacetate and hexane to give 1,1-dimethyl-2-(5-isobutyl-2-morpholinophenyl)guanidine.

Workup

  1. temperaturewas heated at 90°-95° C. for 6 hours
  2. customto yield a residue which
  3. extractionwas extracted with hot hexane
  4. custompurified by chromatography on an alumina column
  5. washeluted with a 2:98 mixture of methanol and dichloromethane
  6. customThe resulting product was crystallised from a 1:3 mixture of ethylacetate and hexane
  7. customThe initial precipitate was removed by filtration
  8. customthe filtrate evaporated to dryness
  9. customto give a residue which
  10. customwas recrystallised from a 1:3 mixture of ethylacetate and hexane

Sources & evidence

ORD record
ord-753360cf439c4082ad8811b0b9d138dd
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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