Triethylamine → N-(but-3-yn-1-yl)pivalamide

HRID 1965964Notes

Reaction equation

HRID 1965964 reaction equation
C(N(CC)CC)C.Cl.[CH2:9]([NH2:13])[CH2:10][C:11]#[CH:12].[C:14](Cl)(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]>C(Cl)Cl>[CH2:9]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][C:11]#[CH:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 12221022But-3-yn-1-amine hydrochloride

Product 1

HCID 56765707N-(but-3-yn-1-yl)pivalamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add triethylamine (3 mL) to a suspension of but-3-ynylamine hydrochloride (200 mg, 2.1 mmol) in DCM (10 mL) and stir for 10 min at room temperature under nitrogen. Add then neat pivaloyl chloride (284.9 μL, 2.31 mmol) and stir at room temperature overnight under nitrogen. Concentrate in vacuo, take up the residue in methanol and filter through a SCX-2 cartridge eluting with methanol to obtain the title compound (265 mg, 65%).

Workup

  1. additionAdd
  2. concentrationConcentrate in vacuo
  3. filtrationfilter through a SCX-2 cartridge
  4. washeluting with methanol

Sources & evidence

ORD record
ord-c765c392aa464df890a302668f943762
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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