Triethylamine → N-methoxy-N-methylpentanamide

HRID 347320Notes

Reaction equation

HRID 347320 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].CCN(CC)CC.[C:13](Cl)(=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17]>C(Cl)Cl>[CH3:2][O:3][N:4]([CH3:5])[C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 3801384N-methoxy-N-methylpentanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 solution (200 mL) containing N-methoxy-N-methylamine hydrochloride (8.09 g, 82.9 mmol) and Et3N (12.6 g, 124 mmol) was added valeryl chloride (10 g, 82.9 mmol) dropwise at room temperature. The resulting solution bubbled vigorously and stirred for 2 hours after which time it was carefully quenched with H2O. The organic layer was separated and washed with 2.0 N NaOH. The organics were extracted with CH2Cl2, dried (MgSO4) and the solvent removed in vacuo. The resulting colorless oil was taken on without further purification.

Workup

  1. customThe resulting solution bubbled vigorously
  2. customwas carefully quenched with H2O
  3. customThe organic layer was separated
  4. washwashed with 2.0 N NaOH
  5. extractionThe organics were extracted with CH2Cl2
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customThe resulting colorless oil was taken on without further purification

Sources & evidence

ORD record
ord-b50b7cd8b6944555a06bbcb581bd93f4
Source dataset
uspto-grants-2007_02
Patent number
US07173134B2

Reaction notes

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