Pyridine → N-[1-(4-bromophenyl)-cyclopropyl]-propionamide

HRID 395161Notes

Reaction equation

HRID 395161 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH2:11])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:12](Cl)(=[O:15])[CH2:13][CH3:14].N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 187101951-(4-Bromophenyl)cyclopropanamine2×

Product 1

HCID 22568996N-[1-(4-bromophenyl)-cyclopropyl]-propionamideYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-bromophenyl)-cyclopropylamine (Intermediate 116, 84 mg, 0.4 mmol) in 4 mL CH2Cl2 at room temperature was added propionyl chloride (43.0 mg, 0.47 mmol) and pyridine (56.0 mg, 0.71 mmol). After stirring 17 hours at room temperature the reaction was quenched by the addition of H2O and extracted with EtOAc. The combined extracts were washed with 10% aqueous HCl, saturated aqueous NaHCO3, and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound 85.0 mg (67%), was isolated by column chromatography (20-50% EtOAc-hexanes) as a colorless solid.

Workup

  1. customwas quenched by the addition of H2O
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with 10% aqueous HCl, saturated aqueous NaHCO3, and saturated aqueous NaCl
  4. dry with materialbefore being dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ba173dc9c2b44f8fa0a8c83bf3f9a03e
Source dataset
uspto-grants-2003_08
Patent number
US06603019B2

Reaction notes

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