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

HRID 347323

Reaction equation

HRID 347323 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-b7434b30502d4142a45c0be72fcadf4f
Source dataset
uspto-grants-2007_02
Patent number
US07173136B2

Linked notes

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