Palmitoyl chloride → 2-methyl-1-[3-(N-hexadecanoyl)aminopropyl]piperidine

HRID 326538Notes

Reaction equation

HRID 326538 reaction equation
[CH3:1][CH:2]1[N:7]([CH2:8][CH2:9][CH2:10][NH2:11])[CH2:6][CH2:5][CH2:4][CH2:3]1.[C:12](Cl)(=[O:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(Cl)Cl>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 8206Palmitoyl chlorideHCID 5202111-(3-Aminopropyl)-2-pipecoline

Product 1

HCID 197352342-methyl-1-[3-(N-hexadecanoyl)aminopropyl]piperidineYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-aminopropyl)-2-pipecoline (1.00 g, 6.40 mmole) in methylene chloride (25 mL) was added palmitoyl chloride (1.73 g, 6.40 mmole) in small portions. The reaction mixture was stirred at room temperature overnight. The reaction mixture was washed twice with saturated aqueous sodium bicarbonate and once with brine. The organic layer was dried over magnesium sulfate and the salts removed by filtration. The solvent was removed under reduced pressure and the residue dried in vacuo to give the title compound (2.12 g, 83%), mp. 48°-50° C. 1H NMR (300 MHz, CDCl3): δ0.883 (3H, t, J=6.5 Hz), 1.136 (3H, d, J=5.5 Hz), 1.254 (24H, bs), 1.60 to 1.70 (4H, m), 2.157 (2H, t, J=7.6 Hz), 2.37 to 2.39 (2H, m), 2.89 to 2.94 (3H, m), 3.24 to 3.27 (1H, m), 3.40 to 3.44 (1H, m), and 7.266 (1H, bs). Analysis calculated for C25H50N2O.1/4H2O C, 75.16; H, 12.61; N, 7.01. Found: C, 75.16; H, 12.69; N, 7.16.

Workup

  1. washThe reaction mixture was washed twice with saturated aqueous sodium bicarbonate and once with brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe salts removed by filtration
  4. customThe solvent was removed under reduced pressure
  5. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-3de9530705cb41b48aec1f80be719574
Source dataset
uspto-grants-1993_12
Patent number
US05270310

Reaction notes

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