3,3,4-Trimethylpiperazin-2-one → 1,2,2-Trimethylpiperazine

HRID 43135Notes

Reaction equation

HRID 43135 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1([CH3:16])[N:13]([CH3:14])[CH2:12][CH2:11][NH:10][C:9]1=O>C1COCC1>[CH3:14][N:13]1[CH2:12][CH2:11][NH:10][CH2:9][C:8]1([CH3:16])[CH3:7]

Participants

4

Reactant 2

HCID 203101823,3,4-Trimethylpiperazin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 219737761,2,2-TrimethylpiperazineYield 46.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

LiAlH4 (1M in THF, 47 mL, 47 mmol, 1.5 equiv) was added to a solution of 3,3,4-trimethyl-piperazin-2-one (Step 107.3) (4.5 g, 32 mmol) in THF (50 mL) at 50° C., under an argon atmosphere. The resulting mixture was stirred for 2 h at 50° C., quenched by addition of acetone, filtered through a pad of celite and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1) to afford 1.9 g of the title compound as a yellow oil. Title compound: ESI-MS: 129.1 [M+H]+.

Workup

  1. customquenched by addition of acetone
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

Sources & evidence

ORD record
ord-f65e500c8ddf407d9963e86fccc769e2
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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