Cyclopropylamine → HCID 18988347, compound

HRID 2396069Notes

Reaction equation

HRID 2396069 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:11]2[N:15]3[CH:16]=[N:17][CH:18]=[C:14]3[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH:19]1([NH2:22])[CH2:21][CH2:20]1>>[CH:19]1([NH:22][C:2]2[CH:3]=[C:4]([CH:11]3[N:15]4[CH:16]=[N:17][CH:18]=[C:14]4[CH2:13][CH2:12]3)[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 18988341HCID 18988341, compound

Product 1

HCID 18988347HCID 18988347, compoundYield 99.6%

Procedure

A mixture of 3.15 g of 5-(3-chloro-4-nitrophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol (preparedas described in EP-A-0,426,225) and 30 ml of cyclopropanamine was stirred for 30 hours at reflux temperature. The reaction mixture was evaporated and the residue was stirred in water. The product was extracted with dichloromethane and the extract was dried, filtered and evaporated. The residue was co-evaporated with methylbenzene, yielding 3.4 g (99.6%) of (±)-N-cyclopropyl-5-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-2-nitrobenzenamine (interm. 6).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. stirringthe residue was stirred in water
  4. extractionThe product was extracted with dichloromethane
  5. customthe extract was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-88560ce5868348e1875a51afbbf37f4e
Source dataset
uspto-grants-1996_02
Patent number
US05491161

Reaction notes

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