N,N-Dimethyl-1,3-propanediamine → Palmitamidopropyl Dimethylamine

HRID 326548

Reaction equation

HRID 326548 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].[C:8](Cl)(=[O:24])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C(Cl)Cl>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH:6][C:8](=[O:24])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 8206Palmitoyl chloride

Product 1

HCID 38313Palmitamidopropyl DimethylamineYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N-dimethyl-1,3-propanediamine (1.00 mL, 7.95 mmole) in methylene chloride (20 mL) was added palmitoyl chloride (2.19 g, 7.97 mmole). The reaction mixture was stirred at room temperature over night. The solvent was removed under reduced pressure and the residue titurated with diethyl ether. The precipitate (2.34 g) was filtered and stirred in saturated aqueous sodium bicarbonate over night. The precipitate was filtered to give the title compound (2.00 g, 74%) as a white solid. Analysis calculated for C21H43H2O 1.25H2O: C: 69.46; H: 12.91; N: 7.72. Found: C: 69.30 C: 9.46; H: 12.91; N: 7.72 Found: C: 69.30, H: 12.13; H: 12.13; N: 7.58.

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationThe precipitate (2.34 g) was filtered
  3. stirringstirred in saturated aqueous sodium bicarbonate over night
  4. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-8d02029d5a5347078fc1ecd36dbfe303
Source dataset
uspto-grants-1993_12
Patent number
US05270310

Linked notes

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