Acetic Acid → Piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3-benzyl ester

HRID 2407496Notes

Reaction equation

HRID 2407496 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([C:25]([O:27]CC2C=CC=CC=2)=[O:26])[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].C(O)(=O)C>CN(C)C=O.O>[CH2:1]([O:8][C:9]([C:11]1([C:25]([OH:27])=[O:26])[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:22])[Cl:23])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5462222PotassiumHCID 67544712Piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3,3-dibenzyl ester

Product 1

HCID 67545923Piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3-benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3,3-dibenzyl ester (5.5 g 15 mmol) in N,N-dimethylformamide (200 mL) cooled with a water/ice bath, is added potassium hydroxyde (0.9 g 85% 14 mmol) dissolved in water (40 mL). The mixture is stirred with cooling for 2 h, allowed to warm to room temperature, acidified with acetic acid (1.05 ew) and concentrated under reduced pressure. Addition of water cristallizes the crude which is filtered, dissolved in ethyl acetate, washed with water, dried over magnesium sulphate and concentrated under reduced pressure. Cristallisation with heptane affords piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3-benzyl ester.

Workup

  1. temperaturewith cooling for 2 h
  2. concentrationconcentrated under reduced pressure
  3. additionAddition of water
  4. filtrationis filtered
  5. dissolutiondissolved in ethyl acetate
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd87a6f2876a4357a8beee832d14cc8f
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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