Methanol → Methyl 4-phenylpiperidine-4-carboxylate hydrochloride

HRID 1682983Notes

Reaction equation

HRID 1682983 reaction equation
Cl.[C:2]1([C:8]2([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17]O.O=S(Cl)[Cl:21]>C(OCC)C>[ClH:21].[CH3:17][O:15][C:14]([C:8]1([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)=[O:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 426142494-Phenylpiperidine-4-carboxylic acid--hydrogen chloride (1/1)

Product 1

HCID 3019446Methyl 4-phenylpiperidine-4-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-phenyl-piperidine-4-carboxylic acid hydrochloride (from example 20.6) (2.67 g, 11 mmol) and methanol (35 mL) were combined. SOCl2 (0.9 mL, 12.34 mmol, 1.1 eq.) was added dropwise. The reaction was heated at reflux for 18 h. The reaction was concentrated in vacuo to obtain a residue. The residue was slurried in diethyl ether, filtered, and the solids were rinsed with diethyl ether to give the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 h
  3. concentrationThe reaction was concentrated in vacuo
  4. customto obtain a residue
  5. filtrationfiltered
  6. washthe solids were rinsed with diethyl ether

Sources & evidence

ORD record
ord-5bdd2c66613f4fe880bd72984130e3bc
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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