Epichlorohydrin → tert-Butyl 4-[(oxiran-2-yl)methyl]piperazine-1-carboxylate

HRID 1768955Notes

Reaction equation

HRID 1768955 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].[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl>CO>[O:18]1[CH2:17][CH:16]1[CH2:14][N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 15491146tert-Butyl 4-[(oxiran-2-yl)methyl]piperazine-1-carboxylateYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(tert-butoxycarbonyl)piperazine (18.6 g, 100 mmol) and epichlorohydrine (10.2 ml, 12.0 g, 130 mmol) in methanol (50 ml) was stirred at room temperature for 24 hours and the solvent was evaporated. The residue was dissolved in 200 ml of ether and the solution was stirred with 10N aqueous NaOH (100 ml) at room temperature for 2 hours. Then the organic layer was separated, washed with brine until neutral, dried over MgSO4 and concentrated to afford the title compound (21.8 g) as a pale yellowish viscous oil, yield: 90.1%.

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in 200 ml of ether
  3. customThen the organic layer was separated
  4. washwashed with brine until neutral,
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-95b3fb7c2a8d423195e25fc4f3b97d88
Source dataset
uspto-grants-1995_01
Patent number
US05380724

Reaction notes

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