Methanol → 1-Boc-4-(3-hydroxypropyl)piperazine

HRID 1644404Notes

Reaction equation

HRID 1644404 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:15][CH2:16][CH2:17][OH:18].C(=O)([O-])[O-].[K+].[K+].CO>C(#N)C.ClCCl>[OH:18][CH2:17][CH2:16][CH2:15][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of tert-butyl piperazine-1-carboxylate (2.75 g, 14.8 mmol), 1-bromo-3-propanol (1.43 mL, 16.2 mmol) and potassium carbonate (2.25 mL, 27.5 mmol) in acetonitrile (75 mL) was heated at 95° C. for 4 hours. The solvent was removed under reduced pressure, and the residue was taken up in dichloromethane (300 mL) and washed with water, brine, dried over sodium sulfate and concentrated under reduced pressure. Chromatography on silica gel with methanol in dichloromethane (0-10%) gave a tan solid 2.88 g (80% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1739c3857c874f7b818952b386f2df41
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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