Hydrochloric Acid → HCID 10494609, compound

HRID 2071015Notes

Reaction equation

HRID 2071015 reaction equation
[BH4-].[Na+].[CH3:3][N:4]([CH3:16])[C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([N:13]([CH3:15])[CH3:14])[CH:12]=1)[C:8]#[N:9].Cl>CCO>[NH2:9][CH2:8][C:7]1[CH:6]=[C:5]([N:4]([CH3:16])[CH3:3])[CH:12]=[C:11]([N:13]([CH3:14])[CH3:15])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydride2×HCID 10607690HCID 10607690, compound

Product 1

HCID 10494609HCID 10494609, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (0.067 g, 1.77 mmol, 3 eq) was added to a stirred solution of 3,5-bis(dimethylamino)benzonitrile (0.1145 g, 0.59 mmol, 1 eq) and CoCl2.6H2O (0.0161 g, 0.059 mmol, 10 mol %) in 5 ml EtOH at 50° C. After 2 h the reaction was not complete. Additional NaBH4 (0.0245 g, 0.64 mmol, 1.1 eq) was added. After 2 h the reaction was cooled to room temperature and 3 N HCl was added to pH=1-2. After stirring for 1 h the reaction was concentrated in vacuo. The residue was extracted with EtOAc (×2). The aqueous layer was adjusted to pH=8-9 with 1 N NaOH. The water was removed in vacuo. The residue was stirred with CHCl3, filtered through Celite, and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo yielding 0.0807 g (0.22 mmol, 37% yield) of the product.

Workup

  1. concentrationwas concentrated in vacuo
  2. extractionThe residue was extracted with EtOAc (×2)
  3. customThe water was removed in vacuo
  4. stirringThe residue was stirred with CHCl3
  5. filtrationfiltered through Celite
  6. dry with materialdried over Na2SO4
  7. filtrationThe inorganics were filtered off
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-62ce9bbbf180477188161f940bbe5e94
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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