Potassium Carbonate → 3-(4-Methyl-1-piperazine)propan-1-ol

HRID 1785092Notes

Reaction equation

HRID 1785092 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[CH3:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:5][CH2:4][CH2:3][CH2:2][N:10]1[CH2:11][CH2:12][N:7]([CH3:6])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 531671-Methylpiperazine

Product 1

HCID 792083-(4-Methyl-1-piperazine)propan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-bromopropanol (20 ml), N-methylpiperazine (29 ml), potassium carbonate (83 g) and ethanol (200 ml)was stirred and heated to reflux for 20 hours. The mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue was triturated under diethyl ether. The resultant mixture was filtered and the filtrate was evaporated. The residue was purified by distillation at about 60-70° C. under about 0.2 mm Hg to give 1-(3-hydroxypropyl)-4-methylpiperazine (17 g); NMR Spectrum: (CDCl3) 1.72 (m, 2H), 2.3 (s, 3H), 2.2-2.8 (m, 8H), 2.6 (t, 2H), 3.8 (t, 2H), 5.3 (br s, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 20 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe residue was triturated under diethyl ether
  6. filtrationThe resultant mixture was filtered
  7. customthe filtrate was evaporated
  8. distillationThe residue was purified by distillation at about 60-70° C. under about 0.2 mm Hg

Sources & evidence

ORD record
ord-b46ce9e6979b4ab6819c04f86aa029d8
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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