Acetone → 4-Isopropylpiperazin-2-one

HRID 922407Notes

Reaction equation

HRID 922407 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:17][C:18](C)=[O:19].[C:21](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CCOC(C)=O>[CH:3]([N:4]1[CH2:5][CH2:6][NH:1][C:18](=[O:19])[CH2:17]1)([CH3:21])[CH3:2]

Participants

6

Reactant 3

HCID 180AcetoneHCID 643495Benzyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 208238784-Isopropylpiperazin-2-oneYield 79%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of piperazin-2-one (1, 0.5 g, 5 mmol) and acetone (0.58 g, 10 mmol) in 1,2-dichloroethane (20 mL) was added sodium triacetoxyborohydride (3.18 g, 15.0 mmol) and the mixture was heated at 70° C. for 2 h. The mixture was diluted with EtOAc/saturated Na2CO3 (100/50 mL), washed with brine (20 mL), dried (Na2SO4), filtered and concentrated to afford the crude title compound (0.56 g, 79%).

Workup

  1. washwashed with brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a63f213975374549b82f26883442c9a4
Source dataset
uspto-grants-2016_03
Patent number
US09278940B2

Reaction notes

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