Cyclopropylamine → tert-Butyl 3-(cyclopropylamino)methyl-4-nitrobenzoate

HRID 2298784Notes

Reaction equation

HRID 2298784 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[CH:19]1([NH2:22])[CH2:21][CH2:20]1>CCO>[CH:19]1([NH:22][CH2:2][C:3]2[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=2[N+:16]([O-:18])=[O:17])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 10335882Tert-butyl 3-(bromomethyl)-4-nitrobenzoate

Product 1

HCID 18378719tert-Butyl 3-(cyclopropylamino)methyl-4-nitrobenzoateYield 86.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

23.7 g of tert-butyl 3-(bromomethyl)-4-nitrobenzoate are suspended in 400 ml of EtOH and treated at 0° C. with 9.0 g of cyclopropylamine. The mixture is stirred for 24 h, concentrated, and the residue is crystallized from petroleum ether. The mother liquor is chromatographed and crystallized. 19 g of the title compound are obtained. MS (DCI) 293 (M+H).

Workup

  1. concentrationconcentrated
  2. customthe residue is crystallized from petroleum ether
  3. customThe mother liquor is chromatographed
  4. customcrystallized

Sources & evidence

ORD record
ord-0c0dd6fa739947dc9f733b90080b0c18
Source dataset
uspto-grants-2002_12
Patent number
US06495545B1

Reaction notes

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