Cyclopropylamine → HCID 771127, compound

HRID 1449393Notes

Reaction equation

HRID 1449393 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7](Cl)=[O:8].[CH:13]1([NH2:16])[CH2:15][CH2:14]1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([NH:16][CH:13]1[CH2:15][CH2:14]1)=[O:8]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 53411290HCID 53411290, compound

Product 1

HCID 771127HCID 771127, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-chlorocinnamoyl chloride (6 g) in dry tolune (100 ml) was added with stirring to a solution of cyclopropylamine (6 g) in dry benzene (50 ml). The reaction mixture was allowed to stand at room temperature overnight, and the solvent was evaporated under reduced pressure. The residue was thoroughly triturated with water containing a small amount of sodium carbonate, washed with water and filtered. Recrystallization of the resulting crude product from ethanol-water (1:10) gave trans 3-chloro-N-cyclopropylcinnamamide (5 g), m.p. 112°-113° C. Elemented analysis, nmr and ir data were all consistent with the assigned structure. TLC gave one spot run on silica gel with 5:1 and with 3:1 hexane:ethanol.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was thoroughly triturated with water containing a small amount of sodium carbonate
  3. washwashed with water
  4. filtrationfiltered
  5. customRecrystallization of the resulting crude product from ethanol-water (1:10)

Sources & evidence

ORD record
ord-c3dc7821fa6a4f168a0ab82019f9f984
Source dataset
uspto-grants-1980_02
Patent number
US04190674

Reaction notes

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