Hydrochloric Acid → 2-Methyl-1-[3-(N-hexadecanoyl)aminopropyl]piperidine hydrochloride

HRID 326539Notes

Reaction equation

HRID 326539 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]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].[ClH:29]>C(OCC)C>[ClH:29].[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]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 313Hydrochloric AcidHCID 197352342-methyl-1-[3-(N-hexadecanoyl)aminopropyl]piperidine

Product 1

HCID 197352372-Methyl-1-[3-(N-hexadecanoyl)aminopropyl]piperidine hydrochlorideYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-methyl-1-[3-(N-hexadecanoyl)aminopropyl]piperidine (0.47 g, 1.2 mmole) in diethyl ether was added an ethereal solution of hydrogen chloride. The reaction mixture was placed in the refrigerator overnight. The precipitate was filtered. The gummy paste was dissolved in methanol and the solvent removed under reduced pressure to give the title compound (0.37 g, 71%) as a pale paste. 1H NMR (300 MHz, CDCl3): mixture of rotamers, major peaks given. δ0.870 (H, t, J=6.7 Hz), 1.243 (24H, bs), 1.533 (3H, d, J=6.4 Hz), 1.59 to 1.66 (2H, m), 1.81 to 1.88 (2H, m), 2.06 to 2.70 (8H, m), 2.74 to 3.10 (2H, m), 3.12 to 3.70 (3H, m), and 7.264 (1H, bs). IR (neat): 2686, 1941, 1649, 1549, 1468, 1379, 1230, and 1123 cm-1. Analysis calculated for C25H51CIN2O.3/4H2O: C, 67.53; H, 11.90; N, 6.30; Cl, 7.97. Found: C, 67.55; H, 11.85; N, 6.29; Cl, 8.04.

Workup

  1. customwas placed in the refrigerator overnight
  2. filtrationThe precipitate was filtered
  3. dissolutionThe gummy paste was dissolved in methanol
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-5cee5c73faa44083adc47af4d2f203ac
Source dataset
uspto-grants-1993_12
Patent number
US05270310

Reaction notes

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