Sodium borohydride → HCID 57436182, compound

HRID 2424404Notes

Reaction equation

HRID 2424404 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[N:3]=1.[BH4-].[Na+]>CO>[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:16][CH2:17]2)[NH:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 49851900Tert-butyl 4-(2-methylquinolin-5-yl)piperazine-1-carboxylate

Product 1

HCID 57436182HCID 57436182, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) and stirred mixture of the tert-butyl 4-(2-methylquinolin-5-yl)piperazine-1-carboxylate prepared in example 6 (4.29 g, 13.1 mmol) and NiCl2.6H2O (0.78 g, 3.3 mmol) in MeOH (250 mL) was added portionwise NaBH4 (3.96 g, 104.8 mmol) and then stirring was continued for 3 h. NaBH4 was added when necessary. The solvent was evaporated in vacuo, the residue was treated with water and then extracted with CH2Cl2. After drying over MgSO4, the solvent was evaporated in vacuo and the residue was purified by column chromatography (eluent CH2Cl2) to afford title compound (2.8 g, 51%). Rf 0.85 (CH2Cl2-MeOH 19:1).

Workup

  1. stirringstirring
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue was treated with water
  4. extractionextracted with CH2Cl2
  5. dry with materialAfter drying over MgSO4
  6. customthe solvent was evaporated in vacuo
  7. customthe residue was purified by column chromatography (eluent CH2Cl2)

Sources & evidence

ORD record
ord-5989ee04f2da4071ba6db2ccb74557b0
Source dataset
uspto-grants-2011_06
Patent number
US07964603B2

Reaction notes

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