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

HRID 647502Notes

Reaction equation

HRID 647502 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][CH2:6][C:7]1[C:12]([O: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>O1CCCC1>[C:1]([NH:5][CH2:6][C:7]1[C:12]([O: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 12074949HCID 12074949, compound

Product 1

HCID 13217542N-{[3-(Benzyloxy)pyridin-2-yl]methyl}acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add dropwise with stirring a solution of 3.5 ml acetyl chloride in 50 ml THF (tetrahydrofuran) to a cooled solution of 10 gm of 2-aminomethyl-3-phenylmethoxypyridine and 7.1 ml triethylamine in 125 ml THF. Warm to room temperature and stir an additional hour. Remove triethylamine hydrochloride by filtration and evaporate the filtrate under reduced pressure. Recrystallize the residue from toluene to obtain 2-acetamidomethyl-3-(phenylmethoxy)pyridine, mp 94°-96°.

Workup

  1. additionAdd dropwise
  2. filtrationRemove triethylamine hydrochloride by filtration
  3. customevaporate the filtrate under reduced pressure
  4. customRecrystallize the residue from toluene

Sources & evidence

ORD record
ord-4d62df5a6a494273b10d5c5f62458d92
Source dataset
uspto-grants-1983_10
Patent number
US04409226

Reaction notes

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