Acetone → 1-(2-Hydroxy-3-n-hexadecyloxypropyl)-4-phenylpiperidine

HRID 1106280Notes

Reaction equation

[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CC1C[CH:16]([O:32][CH:33]([CH2:49][CH:50]1OC1)CCCCCCCCCCCCCCC)[CH2:17][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][CH3:31].CC(C)=[O:56]>>[OH:56][CH:49]([CH2:33][O:32][CH2:16][CH2:17][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][CH3:31])[CH2:50][N:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1

Participants

Reactant 3

HCID 180Acetone

HCID 698734-Phenylpiperidine

HCID 180000852,3-Epoxypropyl-n-hexadecylether

Product 1

HCID 130378071-(2-Hydroxy-3-n-hexadecyloxypropyl)-4-phenylpiperidineYield 50%

Conditions

Temperature: 180 °C

Procedure

4-Phenylpiperidine (1.8 g, 0.011 mol) and 2,3-epoxypropyl-n-hexadecylether (2.98 g, 0.01 mol) were combined and heated to 180° C. for 30 minutes. The reaction mixture was cooled, acetone was added, and the mixture was stirred for 16 hours. The resulting solids were collected and recrystallized from hot acetone to give pure product (2.3 g, 50% yield): mp 64°-65° C.

Workup

temperatureThe reaction mixture was cooled
customThe resulting solids were collected
customrecrystallized from hot acetone

Sources & evidence

ORD record: ord-207c117be1824010b98f68cbc36017a4
Source dataset: uspto-grants-1982_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04312877

Reaction notes

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