Sodium Methoxide → HCID 69431484, compound

HRID 1592854Notes

Reaction equation

HRID 1592854 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([Cl:23])[N:18]=2)[CH3:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:24][O-:25].[Na+]>CO>[ClH:23].[CH3:24][O:25][C:19]1[N:18]=[C:17]([N:15]([CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH3:16])[CH:22]=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 71647831544696-02-8

Product 1

HCID 69431484HCID 69431484, compoundYield 130.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred suspension of 1-t-butoxycarbonyl-4-{[(2-chloropyrimidin-4-yl)(methyl)amino]methyl}piperidine (1.00 g, 2.93 mmol) and sodium methoxide (633 mg, 11.7 mmol) in methanol (7.3 mL) is heated under reflux for 48 hours. Excess methanol is removed in vacuo and the residue is taken into water and ethyl acetate. The phases are separated and the aqueous phase is extracted into ethyl acetate (×3). The combined organic extracts are dried (sodium sulfate), filtered and concentrated in vacuo. The residue is taken into methanol (100 mL) and hydrogen chloride gas is passed through the solution maintaining <20° C. The mixture is kept at this temperature for 2 hours before it is concentrated in vacuo giving 4-{[(2-methoxypyrimidin-4-yl)(methyl)amino]methyl}piperidine hydrochloride (1.04 g, 100%).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 48 hours
  3. customExcess methanol is removed in vacuo
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted into ethyl acetate (×3)
  6. dry with materialThe combined organic extracts are dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. temperaturemaintaining <20° C
  10. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-782cf752fa8749e18f35955d1146ec8a
Source dataset
uspto-grants-2007_11
Patent number
US07294627B2

Reaction notes

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