Acetyl chloride → HCID 117667398, compound

HRID 712739Notes

Reaction equation

HRID 712739 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([C@H:9]([NH2:11])[CH3:10])[CH:6]=[N:7][CH:8]=1.C(N(CC)C(C)C)(C)C.[C:21](Cl)(=[O:23])[CH3:22]>C(Cl)Cl>[Br:2][C:3]1[CH:4]=[C:5]([C@H:9]([NH:11][C:21](=[O:23])[CH3:22])[CH3:10])[CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 117667434HCID 117667434, compound

Product 1

HCID 117667398HCID 117667398, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a vial is added (1R)-1-(5-bromo(3-pyridyl))ethylamine HCl (500 mg, 2.1 mmol) in 2.5 ml of DCM, followed by the addition of N,N-diisopropylethylamine (816 mg, 2.52 mmol). Then acetyl chloride 1M in DCM solution (2.5 ml, 2.5 mmol) is added at 0° C. The reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with DCM, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. Purification by the flash column chromatography affords 273 mg of N-[(R)-1-(5-bromo-pyridin-3-yl)-ethyl]-acetamide.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product
  6. customPurification by the flash column chromatography

Sources & evidence

ORD record
ord-57a49f10f98742139c21244b7c429771
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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