Palmitoyl chloride → Palmitamidopropyl diethylamine

HRID 326540Notes

Reaction equation

HRID 326540 reaction equation
[CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][CH2:6][NH2:7])[CH3:2].[C:10](Cl)(=[O:26])[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][CH2:24][CH3:25]>C(Cl)Cl>[CH2:1]([N:3]([CH2:8][CH3:9])[CH2:4][CH2:5][CH2:6][NH:7][C:10](=[O:26])[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][CH2:24][CH3:25])[CH3:2]

Participants

4

Reactant 2

HCID 8206Palmitoyl chlorideHCID 61011N,N-Diethyl-1,3-propanediamine

Product 1

HCID 19068806Palmitamidopropyl diethylamineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-diethylaminopropylamine (4.13 g, 31.7 mmole) in methylene chloride (50 mL) was added palmitoyl chloride (9.15 g, 33.3 mmole) in small portions. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was dissolved in 1N aqueous sodium hydroxide (90 mL), chloroform (100 mL) and methanol (200 mL). The solution was transferred to a separatory funnel then chloroform (100 mL) and IN aqueous sodium hydroxide (100 mL) was added and the layers separated. The aqueous layer was extracted twice with chloroform (100 mL portions). The solution was transferred to a separatory funnel then chloroform. The organic layer was dried over magnesium sulfate and the salts removed by filtration. The solvent was removed under reduced pressure to give the title compound (11.6 g, 100%) as a gum. 1H NMR (300 MHz, CDCl3): δ0.881 (3H, t, J=6.6 Hz), 1.053 (6H, t, J= 7.1 Hz), 1.252 (24H, bs), 1.56 to 1.67 (2H, m), 2.129 (2H, t, J=7.7 Hz), 2.50 to 2.57 (6H, m), 3.31 to 3.37 (2H, m), and 7.392 (1H, bs). IR (neat): 3307, 3219, 3152, 3085, 2949, 2920, 2850, 1734, 1642, 1082 cm-1. Analysis calculated for C23H48N2O.3/4H2O: C, 74.94; H, 13.12; N, 7.59. Found: C, 74.68; H, 13.11; N, 7.52.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 1N aqueous sodium hydroxide (90 mL)
  3. customThe solution was transferred to a separatory funnel
  4. additionchloroform (100 mL) and IN aqueous sodium hydroxide (100 mL) was added
  5. customthe layers separated
  6. extractionThe aqueous layer was extracted twice with chloroform (100 mL portions)
  7. customThe solution was transferred to a separatory funnel
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. customthe salts removed by filtration
  10. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d854bb0356eb4061bac1c5c2170a9f78
Source dataset
uspto-grants-1993_12
Patent number
US05270310

Reaction notes

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