2-(Pyridin-3-yl)ethan-1-amine → HCID 178477861, compound

HRID 580862Notes

Reaction equation

HRID 580862 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8](=S)[NH:7][C:6]=2[CH:17]=1.[NH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1>C(OCCO)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([NH:18][CH2:19][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[N:7][C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 125357788-Chloro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione

Product 1

HCID 178477861HCID 178477861, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 0.5 g (1.9 mmol) of 8-chloro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione in 10 mL of 2-ethoxyethanol was treated with 0.46 g (3.8 mmol) of 3-(2-aminoethyl)pyridine and heated at reflux overnight. The solvent was removed under reduced pressure and the residue taken up in EtOAc and washed five times with H2O, then saturated NaCl solution. Drying over MgSO4 and removal of the solvent under reduced pressure gave the crude product. Recrystallization from acetone/water gave 0.49 g (74% yield) of the product as a yellow solid, mp 195-196° C. The structure was confirmed by NMR and mass spectroscopy. (m+H)+ =349.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. washwashed five times with H2O
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure
  6. customgave the crude product
  7. customRecrystallization from acetone/water

Sources & evidence

ORD record
ord-8eddc349b20a45a78d2a012779a51de2
Source dataset
uspto-grants-1999_07
Patent number
US05919780

Reaction notes

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