Aluminium lithium hydride → 1-(4-Methoxy-benzyl)-2,2-dimethyl-piperazine

HRID 2391852Notes

Reaction equation

HRID 2391852 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][NH:17][C:16](=O)[C:15]2([CH3:22])[CH3:21])=[CH:11][CH:10]=1>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][C:15]2([CH3:22])[CH3:21])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 669145564-(4-Methoxybenzyl)-3,3-dimethyl-piperazin-2-one

Product 1

HCID 635966481-(4-Methoxy-benzyl)-2,2-dimethyl-piperazineYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

LiAlH4 (1 M in THF, 27.8 mL, 27.8 mmol, 1.5 equiv) was added to a solution of 4-(4-methoxy-benzyl)-3,3-dimethyl-piperazin-2-one (Step 108.3) (4.6 g, 18.5 mmol) in THF (100 mL) at 50° C., under an argon atmosphere. The resulting mixture was stirred for 2 h at 50° C., quenched by sequential addition of H2O (1 mL), 1 N NaOH (1 mL) and H2O (3 mL), filtered through a pad of celite and concentrated to afford 4.0 g of the title compound as a white solid: ESI-MS: 235.2 [M+H]+.

Workup

  1. customquenched by sequential addition of H2O (1 mL), 1 N NaOH (1 mL) and H2O (3 mL)
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f706583ae5e041d3b599b765ef5e9839
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

Loading…