Aluminium lithium hydride → 1,3,3-Trimethylpiperazine

HRID 43153Notes

Reaction equation

HRID 43153 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:12]([N:14]1[CH2:19][CH2:18][NH:17][C:16]([CH3:21])([CH3:20])[C:15]1=O)=O)(C)(C)C>C1COCC1>[CH3:12][N:14]1[CH2:19][CH2:18][NH:17][C:16]([CH3:21])([CH3:20])[CH2:15]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66914586HCID 66914586, compound

Product 1

HCID 223677381,3,3-TrimethylpiperazineYield 71.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

LiAlH4 (1M in THF, 32.5 mL, 32.5 mmol, 1.5 equiv) was added to a solution of 3,3-dimethyl-2-oxo-piperazine-1-carboxylic acid tert-butyl ester (Step 114.3) (4.95 g, 21.7 mmol) in THF (100 mL) at 50° C., under an argon atmosphere. The resulting mixture was stirred for 3 h at 50° C., cooled to 0° C., quenched by addition of acetone and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1) to afford 2 g of the title compound as a yellow oil. Title compound: ESI-MS: 129.1.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by addition of acetone
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

Sources & evidence

ORD record
ord-d86d9ca307a3497ea7425b32fb04dc76
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

Loading…