Water → 1-Benzyl-4-[4-[2-(methoxymethoxy)ethyl]phenyl]piperidin-4-ol

HRID 1059317Notes

Reaction equation

[CH3:1][O:2][CH2:3][O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1.C([Li])CCC.[CH2:19]([N:26]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>O1CCCC1.CCCCCC>[CH2:19]([N:26]1[CH2:31][CH2:30][C:29]([C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][O:4][CH2:3][O:2][CH3:1])=[CH:8][CH:9]=2)([OH:32])[CH2:28][CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: -20 °C

Procedure

Into a solution of 10 g of 4-bromophenethyl methoxymethyl ether in 200 ml of tetrahydrofuran was dropped 28 ml of a 1.6 M solution of n-butyllithium in hexane at −78° C. and the resulting mixture was stirred at the same temperature for 30 minutes. After heating to −20° C., a solution of 7.0 g of 1-benzyl-4-piperidone in tetrahydrofuran (10 ml) was added thereto. The mixture was reacted at the same temperature for 2 hours. After adding water, the resulting mixture was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, 7.6 g of the title compound was obtained as a yellow oily substance.

Workup

customThe mixture was reacted at the same temperature for 2 hours
extractionthe resulting mixture was extracted with ethyl acetate
washwashed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record: ord-7cbe3f2a581441958e1602218d97ed24
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518423B1

Reaction notes

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