Palmitoyl chloride → HCID 19068810, compound

HRID 326547Notes

Reaction equation

HRID 326547 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][NH:6][CH3:7].[C:9](Cl)(=[O:25])[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][CH2:23][CH3:24]>C(Cl)Cl>[C:9]([N:6]([CH3:7])[CH2:5][CH2:4][CH2:3][N:2]([CH3:8])[CH3:1])(=[O:25])[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][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 8206Palmitoyl chlorideHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-

Product 1

HCID 19068810HCID 19068810, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N,N'-trimethyl-1,3-propanediamine (25 g, 0.22 mmole) in methylene chloride (500 mL) was added palmitoyl chloride (57 g, 0.20 mmole) dropwise over 4 hours. After the addition was complete the solvent was removed under reduced pressure. The residue was refluxed in diethyl ether (600 mL) overnight. A portion of the precipitate was collected by filtration and stirred in saturated aqueous sodium bicarbonate (500 mL) overnight. The reaction mixture was extracted three times with chloroform (500 mL portions). The organic layer was dried over magnesium sulfate and the salts removed by filtration. The solvent was removed under reduced pressure. The residue was Kugelrohr distilled to give the title compound as a clear yellow oil. 1H NMR (300 MHz, CDCl3): δrotamers 0.861 (3H, t, J=6.4 Hz), 1.234 (24H, bs) 1.61 to 1.74 (4H, m), 2.196 (6H, s), 2.10 to 2.33 (4H, m) 2.894 and 2.969 (3H, s), 2.767 and 3.139 (2H, t, J=7.3 Hz).

Workup

  1. additionAfter the addition
  2. customwas removed under reduced pressure
  3. temperatureThe residue was refluxed in diethyl ether (600 mL) overnight
  4. filtrationA portion of the precipitate was collected by filtration
  5. extractionThe reaction mixture was extracted three times with chloroform (500 mL portions)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe salts removed by filtration
  8. customThe solvent was removed under reduced pressure
  9. distillationdistilled

Sources & evidence

ORD record
ord-b1194975c75b4c28a49ab7335d3e8f31
Source dataset
uspto-grants-1993_12
Patent number
US05270310

Reaction notes

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