Benzylamine → n-benzyl-3-bromopropanamide

HRID 1248435Notes

Reaction equation

HRID 1248435 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>C(OCC)(=O)C>[CH2:1]([NH:8][C:19](=[O:20])[CH2:18][CH2:17][Br:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 84944Propanoyl chloride, 3-bromo-

Product 1

HCID 236377n-benzyl-3-bromopropanamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of benzylamine (6.49 ml) and triethylamine (8.26 ml) in ethyl acetate (60 ml) was added dropwise to a solution of 3-bromopropionyl chloride (6 ml) in ethyl acetate (10 ml) at 0° C. The reaction mixture was stirred to room temperature for 1 hr. The organic phase was washed with water (2×150 ml), saturated brine (150 ml) and dried over magnesium sulphate. Removal of the solvent produced the amide as a crystalline solid.

Workup

  1. washThe organic phase was washed with water (2×150 ml), saturated brine (150 ml)
  2. dry with materialdried over magnesium sulphate
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-81f45aacaa964f2ca0c63aec49653c04
Source dataset
uspto-grants-1985_06
Patent number
US04524073

Reaction notes

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