Cyclopentylamine → HCID 178484906, compound

HRID 1492247Notes

Reaction equation

HRID 1492247 reaction equation
I.CS[C:4](=[N:18][CH3:19])[NH: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.[CH:20]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+].[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36]>C(O)C>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36].[CH:20]1([NH:25][C:4]([NH:18][CH3:19])=[N:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 2906CyclopentylamineHCID 10340Sodium CarbonateHCID 444972Fumaric AcidHCID 18952225HCID 18952225, compound

Product 1

HCID 178484906HCID 178484906, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-methyl-1-(2-morpholinophenyl)-3-methyl-2-thiopseudourea hydriodide (7.86 g prepared as described in Example 210), cyclopentylamine (2.9 g), anhydrous sodium carbonate (6.36 g) and ethanol (100 ml) was heated in a stainless steel pressure vessel in an oil bath at 110° C. for 24 hours. The reaction mixture was cooled, filtered and the solvent was partially removed. The residue was poured into ice and the resulting mixture extracted with dichloromethane. The extract was dried, filtered and the solvent removed to give a residue which was treated with fumaric acid to give 1-cyclopentyl-2-(2-morpholinophenyl)-3-methylguanidine monofumarate (m.p. 220° C.) which was recrystallised from a 1:1 mixture of methanol and ether.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customthe solvent was partially removed
  4. additionThe residue was poured into ice
  5. extractionthe resulting mixture extracted with dichloromethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto give a residue which

Sources & evidence

ORD record
ord-bb04b03dd28f44e8b0b4d612767f2bd1
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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