Cyclohexylamine, N-methyl-, hydrochloride → HCID 67277979, compound

HRID 1696234Notes

Reaction equation

HRID 1696234 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.Cl.[CH3:12][NH:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C(Cl)(Cl)Cl>[CH:14]1([N:13]([CH3:12])[C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][CH:7]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 3050118Cyclohexylamine, N-methyl-, hydrochlorideHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 67277979HCID 67277979, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

4-Chloro-1H-pyrrolo[2,3-b]pyridine (224 mg) and N-methylcyclohexanamine hydrochloride (1.1g) was combined and stirred at 180° C. for 5 hours under nitrogen atmosphere. After cooled, the reaction mixture was dissolved in chloroform (20ml), washed with saturated aqueous sodium hydrogencarbonate (10ml) and brine, dried over MgSO4, and evaporated in vacuo to give crude red oil. The residue was purified by flash column chromatography over NH-silica gel with a EtOAc as eluant. The fractions containing the object compound were combined, and evaporated under reduced pressure. The residue was washed with ether to give N-cyclohexyl-N-methyl-1H-pyrrolo[2,3-b]pyridin-4-amine (49.8 mg) as a pale yellow solid.

Workup

  1. temperatureAfter cooled
  2. washwashed with saturated aqueous sodium hydrogencarbonate (10ml) and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customto give crude red oil
  6. customThe residue was purified by flash column chromatography over NH-silica gel with a EtOAc as eluant
  7. additionThe fractions containing the object compound
  8. customevaporated under reduced pressure
  9. washThe residue was washed with ether

Sources & evidence

ORD record
ord-3482f81051cf47b092af7c10e5835dde
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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