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

HRID 220833Notes

Reaction equation

HRID 220833 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+].[I-].[K+]>CC(C)=O>[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

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 162178001-Boc-4-(3-hydroxypropyl)piperazineYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of piperazine-1-carboxylic acid tert-butyl ester (26.5 g, 142 mmol) in acetone (300 ml) at room temperature was treated with 3-bromo-propan-1-ol (14.5 ml, 156.2 mmol), potassium carbonate (50 g, 361.8 mmol) and potassium iodide (2.4 g, 14.2 mmol), and the mixture was heated at reflux for 18 h then allowed to cool to room temperature. The suspension was filtered and the filtrate concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 5% methanol:95% dichloromethane) to yield the title compound (27.7 g, 80%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 h
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (eluant; 5% methanol:95% dichloromethane)

Sources & evidence

ORD record
ord-779d6a91de0c4fe28c703216d7279649
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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