4-Pyridinemethanamine → HCID 16460064, compound

HRID 1663082Notes

Reaction equation

HRID 1663082 reaction equation
Cl[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:10][CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1>CN1C(=O)CCC1.CCOC(C)=O>[N:15]1[CH:16]=[CH:17][C:12]([CH2:11][NH:10][C:2]2[N:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 773174-PyridinemethanamineHCID 810792-Chloronicotinonitrile

Product 1

HCID 16460064HCID 16460064, compoundYield 15.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

To a stirred solution of 2-chloro-nicotinonitrile (Aldrich, 10.4 g, 75.06 mmol) in dry NMP (40 ml) was added 4-(aminomethyl)pyridin (15.2 ml, 150.26 mmol). The reaction mixture was heated to 130° C., and stirred at this temperature for 20 hours. The mixture was cooled to room temperature and diluted with EtOAc (500 ml) and washed with saturated aqueous NaHCO3, water and brine. The organic layer was dried (Na2SO4) and evaporated under reduced pressure. The remaining red-brown solid material was recrystallised from ethanol affording the title compound (7.73 g) as an off-white solid. The filtrate was evaporated under reduced pressure, redissolved in 2% methanol/EtOAc (v/v) and filtrated through a pad of silica gel. The filtrate was evaporated under reduced pressure and the residue was recrystallised from ethanol and gave an additional amount of the title compound (2.44 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with saturated aqueous NaHCO3, water and brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customThe remaining red-brown solid material was recrystallised from ethanol affording the title compound (7.73 g) as an off-white solid
  6. customThe filtrate was evaporated under reduced pressure
  7. dissolutionredissolved in 2% methanol/EtOAc (v/v)
  8. filtrationfiltrated through a pad of silica gel
  9. customThe filtrate was evaporated under reduced pressure
  10. customthe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-802ac844bc3b4e0f93eaf28706d75fd6
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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