Potassium Carbonate → 1-(4-(3-Hydroxypropyl)piperazin-1-yl)ethan-1-one

HRID 2180143Notes

Reaction equation

HRID 2180143 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br[CH2:11][CH2:12][CH2:13][OH:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:11][CH2:12][CH2:13][OH:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 837951-Acetylpiperazine

Product 1

HCID 114467711-(4-(3-Hydroxypropyl)piperazin-1-yl)ethan-1-oneYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-acetylpiperazine (3.85 g, 0.03 mol) and 3-bromopropan-1-ol (4 ml) containing potassium carbonate (8.3 g, 60 mmol) in acetonitrile (30 ml) was stirred at 80° C. for 5 hours. The solid was filtered and the filtrate was evaporated. The residue was purified by column chromatography eluting with ethanol/methylene chloride (1/9 followed by 3/7) to give 3-(4-acetylpiperazin-1-yl)propan-1-ol (3.15 g, 56%).

Workup

  1. filtrationThe solid was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography
  4. washeluting with ethanol/methylene chloride (1/9 followed by 3/7)

Sources & evidence

ORD record
ord-ba506c098b12497c84f1a8a69aa3a34f
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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