Acetyl chloride → N-(5-fluoro-pyridin-2-ylmethyl)-acetamide

HRID 245849Notes

Reaction equation

HRID 245849 reaction equation
Cl.Cl.[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][NH2:11])=[N:8][CH:9]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20]>C1COCC1>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][NH:11][C:19](=[O:21])[CH3:20])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67023334(5-Fluoropyridin-2-yl)methanamine dihydrochloride

Product 1

HCID 86677904N-(5-fluoro-pyridin-2-ylmethyl)-acetamideYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a round-bottomed flask, (5-fluoropyridin-2-yl)methylamine dihydrochloride (800 mg, 4.0 mmol) was suspended in THF (15 ml). The suspension was cooled to 0° C. and triethylamine (1.75 ml, 12.6 mmol) was added followed by dropwise addition of acetyl chloride (0.30 ml, 4.22 mmol). After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 2 h. The reaction was quenched with water and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to give 654 mg (97%) of N-(5-fluoro-pyridin-2-ylmethyl)-acetamide as a light brown oil which was used without further purification.

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. customThe reaction was quenched with water
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialthen dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fcf509fa099a474085fc7a1a39ce8db6
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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