Cyclopropylamine → 3-bromo-N-cyclopropyl-4-methylbenzamide

HRID 2357603Notes

Reaction equation

HRID 2357603 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.Cl.CN(C)[CH2:15][CH2:16][CH2:17][N:18]=C=NCC.C1(N)CC1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([NH:18][CH:17]1[CH2:15][CH2:16]1)=[O:7]

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 821303-Bromo-4-methylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 211071523-bromo-N-cyclopropyl-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Bromo-4-methylbenzoic acid (8.35 g, 33 mmol), I H-benzo[d] [1,2,3]triazol-1-ol (4.44 g, 33 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (6.31 g, 33 mmol), and cyclopropylamine (2.5 mL, 36 mmol) were dissolved in dichloromethane (20 mL) and stirred at RT for 16 h. The reaction was diluted with dichloromethane (100 mL), washed 3× with 50 mL of sodium bicarbonate (saturated, aqueous) and 2× with 50 mL of 3 N HCl (aqueous). The organic layer was separated, dried over sodium sulfate, and concentrated via rotovap to give crude product. The crude was purified by chromatography to obtain the title compound. Found MS (ES+): 254(M+H)+.

Workup

  1. washwashed 3× with 50 mL of sodium bicarbonate (saturated, aqueous) and 2× with 50 mL of 3 N HCl (aqueous)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated via rotovap
  5. customto give crude product
  6. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-f1d543e301fa448ea90acad3eb66ae62
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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