Acetyl chloride → N-(Octan-2-yl)acetamide

HRID 610906

Reaction equation

HRID 610906 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][CH:6]([NH2:13])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[CH3:5][CH:6]([NH:13][C:1](=[O:3])[CH3:2])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 127352-Octylamine

Product 1

HCID 529463N-(Octan-2-yl)acetamideYield 74.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of acetyl chloride (7.11 mL, 100 mmol) was added dropwise to an ice water-cooled solution of 1-methylheptyl amine (8.30 g, 64 mmol) and triethylamine (20.91 mL, 150 mmol) in THF (100 mL). The resulting mixture was stirred at RT for 1 h, then was diluted with ethyl acetate and washed twice with 10% HCl, twice with sat aq NaHCO3, and then twice with brine. The organic solution was dried (MgSO4), and concentrated to afford 8.13 g N-(1-methylhept-1-yl)acetamide, a 73% yield.

Workup

  1. washwashed twice with 10% HCl, twice with sat aq NaHCO3
  2. dry with materialThe organic solution was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-526c4c01b4744d06bf952fa8ff467f75
Source dataset
uspto-grants-1999_12
Patent number
US05998466

Linked notes

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