Ethyl Acetate → 4-Cyano-1-(2-hydroxy-3-n-hexadecyloxypropyl)-4-phenylpiperidine

HRID 1106279Notes

Reaction equation

HRID 1106279 reaction equation
[C:1]([C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)#[N:2].O1CC1C[CH:18]([O:34][CH:35]([CH2:51][CH:52]1OC1)CCCCCCCCCCCCCCC)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C(OCC)(=[O:58])C>C(#N)C>[C:1]([C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:5][N:6]([CH2:52][CH:51]([OH:58])[CH2:35][O:34][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:7][CH2:8]1)#[N:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 1811384-Piperidinecarbonitrile, 4-phenyl-HCID 180000852,3-Epoxypropyl-n-hexadecylether

Product 1

HCID 130378024-Cyano-1-(2-hydroxy-3-n-hexadecyloxypropyl)-4-phenylpiperidineYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
185 °C

Procedure

4-Cyano-4-phenylpiperidine (1.1 g, 0.0059 mol) and 2,3-epoxypropyl-n-hexadecylether (1.6 g, 0.0056 mol) were combined and heated to 185° C. for 30 minutes. After cooling, ethyl acetate (20 ml) and acetonitrile (20 ml) were added, and the resulting solid was collected by filtration (1.6 g, 62% yield): mp 69°-70° C.; ir (KBr) 2227 cm-1.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting solid was collected by filtration (1.6 g, 62% yield)

Sources & evidence

ORD record
ord-6fb00ffb2868420ea2f0537e4bffd664
Source dataset
uspto-grants-1982_01
Patent number
US04312877

Reaction notes

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