Chlorotrimethylsilane → Methyl 4-phenylpiperidine-4-carboxylate

HRID 2223731Notes

Reaction equation

HRID 2223731 reaction equation
S([C:5]1C=CC(C)=CC=1)(O)(=O)=O.[C:12]1([C:18]2([C:24]([OH:26])=[O:25])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C[Si](Cl)(C)C>CO>[CH3:5][O:25][C:24]([C:18]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]1)=[O:26]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 545827Methyl 4-phenylpiperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-phenyl-piperidine-4-carboxylic acid tosylate (4.6 g, 20 mmol) in MeOH (25 mL) is added TMSCl (10 mL) and the reaction mixture is stirred at 50° C. for 15 h. The reaction mixture is cooled and evaporated. The residue is taken up in MeOH (5 mL), poured into sat. Na2CO3 (100 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic extracts are dried (Na2SO4), filtered and evaporated to provide the title compound.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customevaporated
  3. additionpoured into sat. Na2CO3 (100 mL)
  4. extractionextracted with CH2Cl2 (3×50 mL)
  5. dry with materialThe combined organic extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0aec7df2661a44adb273920fed2607e2
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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