4-Phenylpiperidine → N-Methyl-2-(4-phenylpiperidin-1-yl)pyrimidin-4-amine

HRID 257749Notes

Reaction equation

HRID 257749 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[C:10]1([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)CCC>[CH3:9][NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:19]2[CH2:20][CH2:21][CH:16]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:17][CH2:18]2)[N:7]=1

Participants

4

Reactant 2

HCID 698734-PhenylpiperidineHCID 137580042-Chloro-N-methylpyrimidin-4-amine

Product 1

HCID 15229206N-Methyl-2-(4-phenylpiperidin-1-yl)pyrimidin-4-amineYield 74.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

Two hundred milliliters of n-butanol was added to 3.0 g (0.02 mole) of 2-chloro-4-methylaminopyrimidine and 8.4 g (0.05 mole) of 4-phenylpiperidine, and the mixture was heated at 130° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and extracted with dichloromethane. The dichloromethane layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 4.0 g (yield 71%) of the desired compound as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with dichloromethane
  3. dry with materialThe dichloromethane layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-84c0254812894f2d88f6c39b965c0463
Source dataset
uspto-grants-1993_11
Patent number
US05264435

Reaction notes

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