Piperidine → 4-Methoxymethyl-5-methyl-6-piperidinopyrimidine

HRID 867887Notes

Reaction equation

HRID 867887 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][O:8][CH2:9][C:10]1[C:15]([CH3:16])=[C:14](Cl)[N:13]=[CH:12][N:11]=1>O1CCCC1>[CH3:7][O:8][CH2:9][C:10]1[C:15]([CH3:16])=[C:14]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 143061604-Methoxymethyl-5-methyl-6-chloropyrimidine

Product 1

HCID 143061614-Methoxymethyl-5-methyl-6-piperidinopyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Piperidine (15 ml) in tetrahydrofuran (40 ml) was added dropwise to a solution of 4-methoxymethyl-5-methyl-6-chloropyrimidine (5 g) in tetrahydrofuran (40 ml). The mixture was heated under reflux for 7 hours and then allowed to stand overnight at room temperature. It was filtered, stripped, and water added to the residual oil. The pH was lowered to 7.5 (HCl) and extracted with chloroform. Extracts were dried (K2CO3) and stripped to give 4-methoxymethyl-5-methyl-6-piperidinopyrimidine, 6.08 g, as an oil, which solidified on cooling to 5° (m.p. 45°-47°). It was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 7 hours
  3. filtrationIt was filtered
  4. additionwater added to the residual oil
  5. extractionextracted with chloroform
  6. dry with materialExtracts were dried (K2CO3)

Sources & evidence

ORD record
ord-cefd035805984ddca80df19c2df7113c
Source dataset
uspto-grants-1988_10
Patent number
US04777172

Reaction notes

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