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

HRID 2068068Notes

Reaction equation

HRID 2068068 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-e9178d9ef4e8435e9427e3e155baed5b
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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