Hydrochloric Acid → 1-(Pyridin-3-yl)ethan-1-amine

HRID 1784921Notes

Reaction equation

HRID 1784921 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:16].[Na+].Cl>CO>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([NH2:16])[CH3:2])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 95893-AcetylpyridineHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 27716881-(Pyridin-3-yl)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-acetylpridine (82.6 mmol) in methanol (200 mL) was added ammonium acetate (1.03 mol) in one portion at room temperature. After the mixture has been stirred for 20 min, sodium cyanoborohydride (57.8 mmol) was added to this mixture. After being stirring for one day, 6 M hydrochloric acid was added to the reaction mixture. The resulting solution was washed with diethyl ether, and then the aqueous phase was basified to PH=10 with potassium hydroxide. The liberated amine was extracted with chloroform, and the combined organic extracts were dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the crude amine was obtained as a colorless oil, which was further purified by distillation under reduced pressure. 1H NMR (300 MHz, CDCl3), δ: 8.552 (d, 1H), 8.453 (dd, 1H), 7.678 (m, 1H), 7.206-7.261 (m, 1H), 4.148 (q, 1H), 1.378 (d, 3H).

Workup

  1. stirringAfter being stirring for one day
  2. washThe resulting solution was washed with diethyl ether
  3. extractionThe liberated amine was extracted with chloroform
  4. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  5. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-14cd69973a56476394dd9346dd853cfe
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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