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

HRID 2070922Notes

Reaction equation

HRID 2070922 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-acetylpyridine (82.6 mmol) in methanol (200 mL) was added ammonium acetate (1.03 mol) in one portion at room temperature. After the mixture was stirred for 20 min, sodium cyanoborohydride (57.8 mmol) was added. After being stirring for one day, 6 M hydrochloric acid was added. 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), d: 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-6de9b2898fb0473daf4c86ce593a86a3
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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