1,4-dibenzyl-piperazine-2-carboxylic acid amide → HCID 10085886, compound

HRID 2245208Notes

Reaction equation

HRID 2245208 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH:15]1[C:27]([NH2:29])=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH:15]1[CH2:27][NH2:29])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 113927221,4-dibenzyl-piperazine-2-carboxylic acid amideHCID 21226445Aluminium lithium hydride

Product 1

HCID 10085886HCID 10085886, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of LAH (0.9 g, 25.9 mmol) in dry THF (150 mL) was added 1,4-dibenzyl-piperazine-2-carboxylic acid amide (4.0 g, 12.93 mmol) and the mixture was stirred under reflux for 20 h (monitored by TLC). The stirred mixture was cooled with an ice-bath and quenched with Rochelle's salt (6 mL), warmed to room temperature, and the suspension was poured over a pad of silica gel (20 mm). The celite was washed with 15% MeOH in CH2Cl2 with 1% NH4OH (3×50 mL) and eluted through pad of silica gel. Th eluent was concentrated under reduced pressure to give the desired product in 99% yield.

Workup

  1. temperatureunder reflux for 20 h (monitored by TLC)
  2. temperatureThe stirred mixture was cooled with an ice-bath
  3. customquenched with Rochelle's salt (6 mL)
  4. additionthe suspension was poured over a pad of silica gel (20 mm)
  5. washThe celite was washed with 15% MeOH in CH2Cl2 with 1% NH4OH (3×50 mL)
  6. washeluted through pad of silica gel
  7. concentrationTh eluent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dd0eb74ff1f04a0083da3cf932c3525d
Source dataset
uspto-grants-2010_03
Patent number
US07683049B2

Reaction notes

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