Hydrochloric Acid → HCID 19969626, compound

HRID 974825Notes

Reaction equation

HRID 974825 reaction equation
O=[C:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N+:5]=1[O-:10].C([O-])(=O)C.[NH4+].C([BH3-])#[N:23].[Na+].Cl>CO>[C:11]1([CH:2]([NH2:23])[CH2:3][C:4]2[N+:5]([O-:10])=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3494282-(1-Oxo-1lambda~5~-pyridin-2-yl)-1-phenylethan-1-oneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19969626HCID 19969626, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ketone (10.72 g, 0.05 mol) prepared in step (a) above was combined with ammonium acetate (38.73 g, 0.5 mol), sodium cyanoborohydride (2.22 g, 0.035 mol) and absolute methanol (200 ml) and stirred at room temperature for 3 days. The mixture was acidified to pH 1 with concentrated HCl, then the methanol was evaporated. The residue was partitioned between water and chloroform and the aqueous layer was separated and basified with solid KOH. The precipitate was extracted into chloroform and the chloroform layer was dried (MgSO4). Concentration of the solvent afforded the amine as a syrup (3.3 g). The amine was converted to the hydrochloride by dissolving in ethyl acetate and adding a saturated solution of hydrogen chloride in isopropanol until acidic. The precipitated solid was filtered and recrystallized from ethanol/ether to give the title compound as a white solid (2.54 g), mp 202°-207° C. (dec).

Workup

  1. customthe methanol was evaporated
  2. customThe residue was partitioned between water and chloroform
  3. customthe aqueous layer was separated
  4. extractionThe precipitate was extracted into chloroform
  5. dry with materialthe chloroform layer was dried (MgSO4)

Sources & evidence

ORD record
ord-7831a1526ee445638e341a5870a69c28
Source dataset
uspto-grants-1997_03
Patent number
US05607935

Reaction notes

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