2-Bromoethanol → (R)-2-(4-acetyl-3-methylpiperazin-1-yl)ethanol

HRID 2381143Notes

Reaction equation

HRID 2381143 reaction equation
Br[CH2:2][CH2:3][OH:4].[C:5]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH3:14])(=[O:7])[CH3:6].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[C:5]([N:8]1[CH2:13][CH2:12][N:11]([CH2:2][CH2:3][OH:4])[CH2:10][C@H:9]1[CH3:14])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 55300442(R)-1-(2-Methylpiperazin-1-YL)ethanone

Product 1

HCID 68499640(R)-2-(4-acetyl-3-methylpiperazin-1-yl)ethanolYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromoethanol (7.34 mL, 103.38 mmol) was added to a stirred mixture of (R)-1-acetyl-2-methylpiperazine (2.94 g, 20.68 mmol) and potassium carbonate (8.57 g, 62.03 mmol) in THF (75 mL). The resulting mixture was stirred at 80° C. for 18 hours before, then filtered and evaporated. The residue was purified by ion exchange chromatography, using an SCX column and eluting with 2M ammonia in methanol. Pure fractions were evaporated to dryness to give (R)-2-(4-acetyl-3-methylpiperazin-1-yl)ethanol (3.74 g, 97%) as a yellow oil.

Workup

  1. filtrationthen filtered
  2. customevaporated
  3. customThe residue was purified by ion exchange chromatography
  4. washeluting with 2M ammonia in methanol
  5. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-490d7fb2983b416590b5ac7b4f06cadd
Source dataset
uspto-grants-2012_09
Patent number
US08258140B2

Reaction notes

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