Cyclopropylamine → HCID 178522504, compound

HRID 1639556Notes

Reaction equation

HRID 1639556 reaction equation
CO[C:3](=[O:15])[NH:4][C:5]1[NH:9][C:8]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:7]=2[N:6]=1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1>CN1CCCC1=O>[CH:16]1([NH:19][C:3]([NH:4][C:5]2[NH:9][C:8]3[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:7]=3[N:6]=2)=[O:15])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 178502034HCID 178502034, compound

Product 1

HCID 178522504HCID 178522504, compoundYield 8.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3 g of methyl(5-hydroxy-1H-benzimidazol-2-yl)carbamate are placed in 15 cm3 of 1-methyl-2-pyrrolidinone and 4.19 g of cyclopropylamine in a 20 cm3 microwave reactor. After the reaction has been hermetically closed, it is placed in the microwave cavity at 130° C. for 25 minutes. The reaction medium is evaporated to dryness under reduced pressure (0.2 to 0.4 kPa) with a bath temperature of 85° C. The residue is taken up in 100 cm3 of water, solidified, filtered off by suction and washed with three times 80 cm3 of water. The cake is taken up in 30 cm3 of a dichloromethane/methanol mixture (90/10 by volume) and the insoluble material is filtered off. This operation is repeated ten times. The filtrates are evaporated to dryness under reduced pressure (2 kPa) at a bath temperature of 50° C. After flash chromatography on a column of silica [eluent: dichloromethane/methanol (90/10 by volume)], 300 mg of 1-cyclopropyl-3-(5-hydroxy-1H-benzimidazol-2-yl)urea are obtained in the form of cream-coloured crystals, the characteristics of which are as follows:

Workup

  1. customAfter the reaction has been hermetically closed
  2. customThe reaction medium is evaporated to dryness under reduced pressure (0.2 to 0.4 kPa) with a bath temperature of 85° C
  3. filtrationfiltered off by suction
  4. washwashed with three times 80 cm3 of water
  5. filtrationthe insoluble material is filtered off
  6. customThe filtrates are evaporated to dryness under reduced pressure (2 kPa) at a bath temperature of 50° C

Sources & evidence

ORD record
ord-64e2185381924c0c8949d872c8da7610
Source dataset
uspto-grants-2012_02
Patent number
US08110571B2

Reaction notes

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