Piperidin-4-ol → 1-[2-Hydroxy-2-(5-phenyl-1,2-oxazol-3-yl)ethyl]piperidin-4-ol

HRID 1580049Notes

Reaction equation

HRID 1580049 reaction equation
[O:1]1[CH2:3][CH:2]1[C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][N:5]=1.[OH:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>>[OH:1][CH:2]([C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][N:5]=1)[CH2:3][N:19]1[CH2:20][CH2:21][CH:16]([OH:15])[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 79341Piperidin-4-olHCID 13034600HCID 13034600, compound

Product 1

HCID 30434821-[2-Hydroxy-2-(5-phenyl-1,2-oxazol-3-yl)ethyl]piperidin-4-olYield 50.4%

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(1,2-epoxyethyl)-5-phenylisoxazole (580 mg) and 4-hydroxypiperidine (625 mg) is stirred for 0.5 hour at 80°C and then the mixture is subjected to a column chromatography using silica gel to give 3-[1-hydroxy-2-(4-hydroxypiperidino ) ethyl]-5-phenylisoxazole (450 mg). Recrystallization from ethyl acetate-hexane gives colorless prisms (259 mg). M. p. 117-119°C.

Sources & evidence

ORD record
ord-4c5aa5070e9d4233a25bfb35fcc9d9ae
Source dataset
uspto-grants-1976_01
Patent number
US03932426

Reaction notes

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