Cyclopropylamine → 2-Propenamide, 3-(3-bromophenyl)-N-cyclopropyl-, (E)-

HRID 1449390Notes

Reaction equation

HRID 1449390 reaction equation
[Br: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>C1(C)C=CC=CC=1>[Br: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 14959106trans 3-Bromocinnamoyl chloride

Product 1

HCID 8220092-Propenamide, 3-(3-bromophenyl)-N-cyclopropyl-, (E)-Yield 90.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of trans 3-bromocinnamoyl chloride (12.2 g) in dry toluene (150 ml) was added dropwise (rapidly) with rapid stirring to a solution of cyclopropylamine (6.3 g) in dry toluene (150 ml). The reaction mixture was stirred at room temperature for 2 hours, then at 30°-35° C. for an additional hour; and the solvent and excess amine were removed under reduced pressure. The residue was triturated with water to remove cyclopropylamine hydrochloride. The product was filtered, washed with dilute hydrochloric acid and then with water. It was then recrystallized from ethanol:water (1:10) to give white crystalline trans 3-bromo-N-cyclopropylcinnamamide (12 g), m.p. 110°-111° C. Elemental analysis, NMR and 1R 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. waitat 30°-35° C. for an additional hour
  2. customand the solvent and excess amine were removed under reduced pressure
  3. customThe residue was triturated with water
  4. customto remove cyclopropylamine hydrochloride
  5. filtrationThe product was filtered
  6. washwashed with dilute hydrochloric acid
  7. customIt was then recrystallized from ethanol:water (1:10)

Sources & evidence

ORD record
ord-e149e2f0c44b4b1eb9cb638015eb0fed
Source dataset
uspto-grants-1980_02
Patent number
US04190674

Reaction notes

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