Sodium borohydride → HCID 12378777, compound

HRID 1501286Notes

Reaction equation

HRID 1501286 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:6]=[N:7][CH2:8][CH:9]([O:12][CH3:13])[O:10][CH3:11].[BH4-].[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:6][NH:7][CH2:8][CH:9]([O:10][CH3:11])[O:12][CH3:13]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 1125379939964-87-9

Product 1

HCID 12378777HCID 12378777, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The imine 7 (12.01 g, 47.47 mmol) was dissolved in ethanol (200 mL), and NaBH4 (3.61 g, 95.4 mmol) was added over 0.5 h while the reaction mixture was stirred at reflux. The reaction mixture was diluted with water (200 mL). The amine was extracted into chloroform (250 mL) and the extract washed with water (2×150 mL) and brine (150 mL), dried (Na2SO4) and concentrated to provide clear colorless oil (10.65 g, 88%). 1H NMR (300 MHz, CDCl3) δ 6.78-6.84 (m, 3H), 4.44 (t, J=5.4 Hz, 1H), 3.88 (s, 3H), 3.86 (s, 3H), 3.70 (s, 2H), 3.33 (s, 6H), 2.69 (d, J=5.4 Hz, 2H).

Workup

  1. temperatureat reflux
  2. extractionThe amine was extracted into chloroform (250 mL)
  3. washthe extract washed with water (2×150 mL) and brine (150 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-94007036137043398b48ed1dd1852e5f
Source dataset
uspto-grants-2015_12
Patent number
US09206193B2

Reaction notes

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