Sodium Carbonate → Piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3,3-dibenzyl ester

HRID 2407495Notes

Reaction equation

HRID 2407495 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:16][CH2:15][CH2:14][N:13](CC2C=CC=CC=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:41]([O:43][CH2:44][C:45]([Cl:48])([Cl:47])[Cl:46])=[O:42]>C(Cl)(Cl)Cl>[CH2:27]([O:26][C:24]([C:11]1([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:16][CH2:15][CH2:14][N:13]([C:41]([O:43][CH2:44][C:45]([Cl:48])([Cl:47])[Cl:46])=[O:42])[CH2:12]1)=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 675458771-Benzylpiperidine-3,3-dicarboxylic acid 3,3-dibenzyl ester

Product 1

HCID 67544712Piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3,3-dibenzyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 1-benzylpiperidine-3,3-dicarboxylic acid 3,3-dibenzyl ester (19.6 g 41.8 mmol) and sodium carbonate (5.1 g, 48.1 mmol) in chloroform cooled with a water/ice bath, is added 2,2,2-trichloroethyl chloroformate (11 g, 51.8 mmol). The mixture is stirred overnight at room temperature and concentrated under reduced pressure. The residue is dissolved in diethyl oxide, washed with water, dried over magnesium sulphate and concentrated under reduced pressure to give piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3,3-dibenzyl ester which cristallizes upon standing.

Workup

  1. temperaturecooled with a water/ice bath
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue is dissolved in diethyl oxide
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4cb6b020a8d14a08bc237041a6ecb240
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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