Dichloromethane → HCID 69619505, compound

HRID 1791369Notes

Reaction equation

HRID 1791369 reaction equation
[Cl:1]CCl.[CH2:4]([O:6][C:7]([CH:9]1[CH2:14][C:13]([CH3:15])=[CH:12][CH2:11][N:10]1C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:8])[CH3:5].ClC(OC(Cl)C)=O>[Pd].CO>[ClH:1].[CH2:4]([O:6][C:7]([CH:9]1[CH2:14][CH:13]([CH3:15])[CH2:12][CH2:11][NH:10]1)=[O:8])[CH3:5]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 5213051-Chloroethyl chloroformateHCID 12117194HCID 12117194, compound

Product 1

HCID 69619505HCID 69619505, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a dichloromethane (50 mL) solution of 1-benzhydryl-4-methyl-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid ethyl ester *(5.0 g, 14.9 mmol), 1-chloroethyl chloroformate (2.13 g, 14.9 mmol) was added at room temperature under argon. The reaction mixture was stirred overnight. After the reaction mixture was mixed with methanol (50 mL) and refluxed for an hour, cooled down to room temperature and 10% Pd/C (2 g) was added to reaction mixture and stirred under hydrogen overnight. The reaction mixture was filtered through celite and 1 M HCl in ether (15 mL) was added. After concentration, the residue was triturated with acetone, filtered to 2.03 g (65.5%) of 4-methyl-piperidine-2-carboxylic acid ethyl ester hydrochloride.

Workup

  1. temperaturerefluxed for an hour
  2. stirringstirred under hydrogen overnight
  3. filtrationThe reaction mixture was filtered through celite and 1 M HCl in ether (15 mL)
  4. additionwas added
  5. concentrationAfter concentration
  6. customthe residue was triturated with acetone
  7. filtrationfiltered to 2.03 g (65.5%) of 4-methyl-piperidine-2-carboxylic acid ethyl ester hydrochloride

Sources & evidence

ORD record
ord-8d3afec238354a63b559e2c8eeda65b0
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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