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

HRID 127254Notes

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-9679826e97e14bcd854a82e8314045c7
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04255426

Reaction notes

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