Dimethylamine → N,N-dimethylpent-4-ynamide

HRID 2223453Notes

Reaction equation

HRID 2223453 reaction equation
[CH3:1][NH:2][CH3:3].C(N(CC)CC)C.CN(C)CCCN=C=NCC.[C:22]([OH:28])(=O)[CH2:23][CH2:24][C:25]#[CH:26]>C(Cl)Cl>[CH3:1][N:2]([CH3:3])[C:22](=[O:28])[CH2:23][CH2:24][C:25]#[CH:26]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 224644-Pentynoic acid

Product 1

HCID 17851574N,N-dimethylpent-4-ynamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylamine (2 M solution in tetrahydrofuran, 8.53 ml), triethylamine (2.59 ml), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (3221 mg), were added to a solution of 4-pentynoic acid (552 mg) in methylene chloride (150 ml) and this reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was washed successively with 1 N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure to give the title compound (129 mg). The obtained compound was used in the following reaction without further purification.

Workup

  1. washThe reaction mixture was washed successively with 1 N hydrochloric acid
  2. dry with materiala saturated aqueous sodium hydrogencarbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-87100b46740f4e549cc1499e546280bd
Source dataset
uspto-grants-2008_05
Patent number
US07375204B2

Reaction notes

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