Sodium Bicarbonate → tert-butyl (2S)-2-methyl-4-[2-methyl-4-(methylamino)benzyl]piperazine-1-carboxylate

HRID 644734Notes

Reaction equation

HRID 644734 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([NH:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:12][C@H:13]1[CH2:18][NH:17][CH2:16][CH2:15][N:14]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH3:1][C:2]1[CH:9]=[C:8]([NH:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH2:4][N:17]1[CH2:16][CH2:15][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:13]([CH3:12])[CH2:18]1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylateHCID 450836492-Methyl-4-(methylamino)benzaldehyde

Product 1

HCID 59262129tert-butyl (2S)-2-methyl-4-[2-methyl-4-(methylamino)benzyl]piperazine-1-carboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 2-methyl-4-(methylamino)benzaldehyde (D93) (0.397 g) and 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (0.533 g, 2.66 mmol) in 1,2-DCE (35 mL) was added sodium tri(acetoxy)borohydride (0.847 g, 4.00 mmol) and the reaction stirred at room temperature overnight. Saturated aqueous NaHCO3 (30 mL) was added and the mixture was stirred for 4 h. The reaction mixture was extracted with DCM and the organics were dried and concentrated to give the crude product which was purified by column chromatography. Elution with ether/petroleum ether gave the title compound as a colourless oil (0.328 g).

Workup

  1. stirringthe mixture was stirred for 4 h
  2. extractionThe reaction mixture was extracted with DCM
  3. customthe organics were dried
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by column chromatography
  7. washElution with ether/petroleum ether

Sources & evidence

ORD record
ord-65322071637a4902afa7c0362b7d491e
Source dataset
uspto-grants-2010_04
Patent number
US07700599B2

Reaction notes

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