Acetyl chloride → N-{[3-(2-Phenylethyl)pyridin-2-yl]methyl}acetamide

HRID 647504Notes

Reaction equation

HRID 647504 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][CH2:6][C:7]1[C:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=[CH:9][N:8]=1.C(N(CC)CC)C>C1COCC1>[C:1]([NH:5][CH2:6][C:7]1[C:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=[CH:9][N:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 20485150HCID 20485150, compound

Product 1

HCID 20485147N-{[3-(2-Phenylethyl)pyridin-2-yl]methyl}acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add dropwise with stirring a solution of 1.24 gm acetyl chloride in 10 ml THF to a cooled solution of 3.2 gm of 2-aminomethyl-3-(2-phenylethyl)pyridine and 2.3 ml triethylamine in 100 ml THF. Warm the reaction mixture to room temperature and then stir for an additional 0.5 hour. Filter off the triethylamine hydrochloride and evaporate the filtrate under reduced pressure. Chromatograph on silica gel using 40% THF in chloroform to obtain 2-acetamidomethyl-3-(2-phenylethyl)pyridine.

Workup

  1. additionAdd dropwise
  2. filtrationFilter off the triethylamine hydrochloride
  3. customevaporate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-79e05b060aae480e9679c512c85c0cac
Source dataset
uspto-grants-1983_10
Patent number
US04409226

Reaction notes

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