Potassium Carbonate → 1-Boc-4-(3-hydroxypropyl)piperazine

HRID 916427Notes

Reaction equation

HRID 916427 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:15][CH2:16][CH2:17][OH:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH2:17][OH:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 162178001-Boc-4-(3-hydroxypropyl)piperazineYield 91.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-tert-butoxycarbonylpiperazine (1.0 g, 5.37 mmol), 3-bromo-1-propanol (0.49 ml, 5.37 mmol) and potassium carbonate (1.86 g, 13.4 mmol) was heated at reflux in acetonitrile (10 ml) for 1.5 hours. The mixture was concentrated under reduced pressure and column chromatography of the residue, eluting with 2% methanol/methylene chloride, gave 1-tert-butoxycarbonyl-4-(3-hydroxypropyl)piperazine (1.2 g, 91%).

Workup

  1. temperaturewas heated
  2. concentrationThe mixture was concentrated under reduced pressure and column chromatography of the residue
  3. washeluting with 2% methanol/methylene chloride

Sources & evidence

ORD record
ord-2c626f246e9e43e58e2322e67afa7ec0
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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