Hydrochloric Acid → HCID 59569716, compound

HRID 2070947Notes

Reaction equation

HRID 2070947 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][NH2:9])=[CH:6][C:5]([C:10]([CH3:12])=[CH2:11])=[C:4]([CH3:13])[N:3]=1.[BH4-].[Na+].Cl>CCO>[CH:10]([C:5]1[CH:6]=[C:7]([CH2:8][NH2:9])[C:2]([CH3:1])=[N:3][C:4]=1[CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 68669579HCID 68669579, compound

Product 1

HCID 59569716HCID 59569716, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude (2,6-dimethyl-5-(prop-1-en-2-yl)pyridin-3-yl)methanamine and 120 mg (0.505 mmol) of CoCl2.6H2O in 5 mL of EtOH at 50° C. was added 115 mg of NaBH4 in 2 portions. After 2 h, 5N HCl was added to a pH=1 and stirring was continued until the bubbling ceased. The mixture was concentrated, and NH4OH was added to pH=9. Some water was added, and the aqueous layer was extracted with the extract of (40 mL CHCl3: 5 mL MeOH: 5 mL H2O). The combined extracts were dried over Na2SO4, filtered, and concentrated to give the crude (5-isopropyl-2,6-dimethylpyridin-3-yl)methanamine which was used without further purification.

Workup

  1. concentrationThe mixture was concentrated
  2. additionNH4OH was added to pH=9
  3. additionSome water was added
  4. extractionthe aqueous layer was extracted with the
  5. extractionextract of (40 mL CHCl3: 5 mL MeOH: 5 mL H2O)
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c799af08fb3d43c4afad7473fad1f059
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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