Methylamine → 3-(4-bromophenyl)-N-methylpropanamide

HRID 735548Notes

Reaction equation

HRID 735548 reaction equation
C[CH2:2][N:3]=C=NCCCN(C)C.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([OH:23])=O)=[CH:15][CH:14]=1.C1C=CC2N(O)N=NC=2C=1.NC>CN(C=O)C.O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([NH:3][CH3:2])=[O:23])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27356093-(4-Bromophenyl)propionic acid

Product 1

HCID 178950553-(4-bromophenyl)-N-methylpropanamideYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

EDAC (1.56 g, 8.1 mmol) was added in one portion to 3-(4-bromophenyl)propanoic acid (2.5 g, 7.4 mmol) and HOBt (1.1 g, 8.1 mmol) in DMF (6 mL) and the reaction mixture was stirred for 2 h. The reaction mixture was cooled to 0° C. and NH2Me (2.0 M in MeOH, 29 mL, 58 mmol) was added dropwise. The solution was stirred at 0° C. for 30 min and 10 h at ambient temperature. The reaction mixture was diluted with water (25 mL), extracted with diethyl either (3×50 mL). The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 22A (1.7 g, 67%) as an off-white solid. MS (ESI) m/z 242.22/244.22 (M+H)+.

Workup

  1. stirringThe solution was stirred at 0° C. for 30 min and 10 h at ambient temperature
  2. extractionextracted with diethyl either (3×50 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9be598a238945c6b1e134e39a212a04
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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