Isobutylene oxide → 1-(4-(6-Chloro-3-pyridinyl)-1-piperazinyl)-2-methyl-2-propanol

HRID 875984Notes

Reaction equation

HRID 875984 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:14][C:15]1([O:18][CH2:17]1)[CH3:16]>CO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][C:15]([CH3:17])([OH:18])[CH3:16])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11208Isobutylene oxide2×HCID 99643631-(6-Chloropyridin-3-yl)piperazine

Product 1

HCID 582996541-(4-(6-Chloro-3-pyridinyl)-1-piperazinyl)-2-methyl-2-propanolYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-(6-chloropyridin-3-yl)piperazine (0.600 g, 3.04 mmol) in methanol (1.5 mL) was added dropwise isobutylene oxide (0.274 mL, 3.04 mmol). The reaction was left to stir at room temperature overnight. An additional 0.15 equivalents of isobutylene oxide were added and the reaction was placed in a 55° C. oil bath overnight. Solvent was removed in vacuo. Silica gel chromatography (gradient elution 2 to 10% methanol in DCM) afforded compound 251 (0.450 g, 55.0% yield). 1H NMR (400 MHz, CDCl3) δ 0.95-1.50 (m, 7 H) 2.23-3.61 (m, 9 H) 7.12-7.24 (m, 2 H) 8.03 (br. s., 1 H) ppm.

Workup

  1. waitThe reaction was left
  2. customwas placed in a 55° C.
  3. customovernight
  4. customSolvent was removed in vacuo
  5. washSilica gel chromatography (gradient elution 2 to 10% methanol in DCM)

Sources & evidence

ORD record
ord-1ea9ac50913c4688a5ab5f9bb75d878f
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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