Isobutylene oxide → 1-{4-[(Dibenzylamino)methyl]piperidin-1-yl}-2-methylpropan-2-ol

HRID 1743818Notes

Reaction equation

[CH2:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][C:24]1([CH3:27])[CH2:26][O:25]1>CO.O1CCCC1>[CH2:16]([N:8]([CH2:9][CH:10]1[CH2:11][CH2:12][N:13]([CH2:23][C:24]([CH3:27])([OH:25])[CH3:26])[CH2:14][CH2:15]1)[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of N,N-dibenzyl-N-(piperidin-4-ylmethyl)amine (EXAMPLE 4, Step 3, 3.3 g, 11.21 mmol) and 2,2-dimethyloxirane (12.1 mL, 134.5 mmol) in methanol (40 mL) and tetrahydrofuran (5 mL) was heated at 40° C. with stirring for 17 h. The volatile components were removed and the residue was purified by flash column chromatography on amine gel eluting with hexane/ethyl acetate (50:1) to afford 3.0 g (73%) of the title compound as a colorless amorphous.

Workup

customThe volatile components were removed
customthe residue was purified by flash column chromatography on amine gel
washeluting with hexane/ethyl acetate (50:1)

Sources & evidence

ORD record: ord-a16cb4ec55af473896cfe1be6452dabe
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07012080B2

Reaction notes

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