Acetic Acid → HCID 66967695, compound

HRID 1362115Notes

Reaction equation

HRID 1362115 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=O.CC(O)=O.[BH3-]C#N.[Na+]>CO.C([O-])(O)=O.[Na+]>[CH2:17]([O:16][C:12](=[O:15])[CH2:13][NH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([CH3:11])[CH2:9][CH2:10]1)[CH3:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 70211Ethyl oxoacetateHCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 66967695HCID 66967695, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4-(3-aminopropyl)-1-methylpiperazine (3.1 mL, 20 mmol) in MeOH (50 mL) was cooled in an ice bath and treated with ethyl glyoxylate (50% solution in toluene, 5.6 mL, 27 mmol) and AcOH (3 mL). After stirring for 15 min, NaBH3CN (1.37 g, 21.8 mmol) was added and the mixture was allowed to stir for 7 h while slowly warming to room temperature. The mixture was diluted with saturated aqueous NaHCO3 (150 mL) and then extracted with EtOAc (3×100 mL) followed by CH2Cl2 (3×100 mL). The combined CH2Cl2 layers were dried over Na2SO4, filtered and the solvent was removed in vacuo to give the title compound (1.81 g, 38%) as a colorless oil: MS (ESI) m/e 244 (M+H)+.

Workup

  1. stirringto stir for 7 h
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialThe combined CH2Cl2 layers were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ff134c5721a34500b75ba7e14f626b95
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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