Palmitoyl chloride → HCID 19735238, compound

HRID 326546Notes

Reaction equation

HRID 326546 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][NH:6][CH3:7].[C:9]([Cl:26])(=[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>[ClH:26].[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 19735238HCID 19735238, 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. The precipitate was collected and a portion crystallized from ethyl acetate to give the title compound as a white solid. mp. 105.3°-107.9° C. 1H NMR (300 MHz, CD3OD): δ0.894 (3H, t, J=6.5 Hz), 1.282 (2H, bs), 1.56 to 1.64 (2H, m), 1.89 to 1.99 (2H, m), 2.411 (2H, t, J=7.1 Hz), 2.873 (6H, s), 3.071 (3H, s) and 3.460 ppm (2H, t, J=6.4 Hz). Analysis calculated for C22H48ClN2O: C, 67.56; H, 12.12; N, 7.16; Cl, 9.07. Found: C, 67.37; H, 12.03; N, 7.10; Cl, 9.20.

Workup

  1. additionAfter the addition
  2. customwas removed under reduced pressure
  3. temperatureThe residue was refluxed in diethyl ether (600 mL) overnight
  4. customThe precipitate was collected
  5. customa portion crystallized from ethyl acetate

Sources & evidence

ORD record
ord-7c1badefc2874e7fae2c6d6ab5bf4b18
Source dataset
uspto-grants-1993_12
Patent number
US05270310

Reaction notes

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