Water → 4-(5-Methyl-4-phenyl-4H-1,2,4-triazol-3-yl)-1-(2-phenylethyl)-4-piperidinol

HRID 1979635

Reaction equation

[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:5]=[N:4][N:3]=1.C([Li])CCC.[C:18]1([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C1COCC1>[CH3:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:29]2([OH:32])[CH2:30][CH2:31][N:26]([CH2:25][CH2:24][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:27][CH2:28]2)=[N:4][N:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1.6 g of 3-methyl-4-phenyl-4H-1,2,4-triazole (10 mmol) in 15 ml of THF at -78° C. is added 7.0 ml of n-butyllithium (1.6N in hexane). The mixture is stirred for 50 minutes before a solution of 2.44 g of N-(2-phenylethyl)-4-piperidinone in 12 ml of THF is charged into the flask. After stirring for 30 minutes at -78° C. and then 1 hour at -20° C. the mixture is poured into cold water and is extracted three times with chloroform. The combined chloroform extracts are washed twice with water, brine, dried over sodium sulfate and concentrated in vacuo to yield an amber oil.

Workup

additionis charged into the flask
extractionis extracted three times with chloroform
washThe combined chloroform extracts are washed twice with water, brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customto yield an amber oil

Sources & evidence

ORD record: ord-0ad527f8973443869b5bf86e21387555
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04481360

Linked notes

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