Water → N-[(4-tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methyl]cyclopentanamine

HRID 70721Notes

Reaction equation

HRID 70721 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3]C1.C(=O)(O)[O-].[Na+].[C:13]([C:17]1[CH:22]=[CH:21][C:20]([CH:23](Cl)[C:24]2[N:29]=[C:28]([O:30][CH3:31])[C:27]([Cl:32])=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].O>C(#N)C>[C:13]([C:17]1[CH:22]=[CH:21][C:20]([CH:23]([C:24]2[CH:25]=[CH:26][C:27]([Cl:32])=[C:28]([O:30][CH3:31])[N:29]=2)[NH:7][CH:1]2[CH2:3][CH2:4][CH2:5][CH2:6]2)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7965CyclohexylamineHCID 516892Sodium BicarbonateHCID 673982706-[(4-Tert-butylphenyl)(chloro)methyl]-3-chloro-2-methoxypyridine

Product 1

HCID 67399418N-[(4-tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methyl]cyclopentanamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Cyclohexylamine (0.30 mL) and sodium bicarbonate (259 mg) were sequentially added to a solution of 6-[(4-tert-butylphenyl)(chloro)methyl]-3-chloro-2-methoxypyridine (200 mg) in acetonitrile (4 mL) at room temperature, and then the mixture was heated under reflux for six hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:50→1:10) to give N-[(4-tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methyl]cyclopentanamine as a pale yellow amorphous (201 mg, 87%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for six hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customafter which the solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:50→1:10)

Sources & evidence

ORD record
ord-c1b699ce134941fbbd8f34758385d5eb
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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