Dimethylamine, hydrochloride → 3-(4-bromophenyl)-N,N-dimethylpropanamide

HRID 1988613Notes

Reaction equation

HRID 1988613 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[C:13](N1C=CN=C1)([N:15]1C=CN=[CH:16]1)=O.Cl.CNC.C(N(C(C)C)CC)(C)C>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:15]([CH3:16])[CH3:13])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 27356093-(4-Bromophenyl)propionic acid

Product 1

HCID 577628213-(4-bromophenyl)-N,N-dimethylpropanamideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(4-bromophenyl)propionic acid (1.0 g, 4.37 mmol) in dichloromethane (30 ml) was treated in one portion with solid 1,1′-carbonyldiimidazole (707 mg, 4.36 mmol). This mixture was allowed to stir at room temperature for 15 minutes. Dimethylamine hydrochloride (360 mg, 4.42 mmol) was then added followed by diisopropylethylamine (0.76 ml, 4.4 mmol) and the stirring continued for 1 hour at room temperature. The reaction mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was dried over sodium sulphate and evaporated under reduced pressure to give the title compound as a colourless oil (972 mg, 87%).

Workup

  1. waitthe stirring continued for 1 hour at room temperature
  2. customThe reaction mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5ace3c3bd3714ad1a8e4d53fad6eeaeb
Source dataset
uspto-grants-2010_01
Patent number
US07642256B2

Reaction notes

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