Potassium Carbonate → HCID 67544413, compound

HRID 2407489Notes

Reaction equation

HRID 2407489 reaction equation
[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:11][CH2:12]Cl)[CH2:8]CCl)([CH3:4])([CH3:3])[CH3:2].[C:15]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:27])[CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].[C:36](=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:20]([O:19][C:17]([C:16]1([C:15]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[CH2:36][CH2:12][CH2:11][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:14])[CH2:8]1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 84754Dibenzyl malonateHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Product 1

HCID 67544413HCID 67544413, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalyst2×HCID 1140TolueneSolvent

Procedure

A mixture of N,N-bis(2-chloroethyl)carbamic acid tert-butyl ester (1.22 g 5 mmol), dibenzyl malonate (1.42 g 5 mmol), potassium carbonate (1.38 g 10 mmol) and tetrabutylammonium bromide (0.5 g 1.55 mmol) in toluene (20 mL) is heated under reflux. Additional portion of tetrabutylammonium bromide (0.5 g 1.55 mmol) is added after 2 h reflux (twice). After further heating for 2 h (overall 6 h heating) the mixture is cooled back to room temperature and diethyl oxyde is added (50 mL). The organic phase is washed with water, dried and concentrated under reduced pressure. Purification by column chromatography affords piperidine-1,3,3-tricarboxylic acid 1-tert-butyl 3,3-dibenzyl ester as an oil.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperaturereflux (twice)
  4. temperatureAfter further heating for 2 h
  5. temperature(overall 6 h heating) the mixture
  6. additiondiethyl oxyde is added (50 mL)
  7. washThe organic phase is washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customPurification by column chromatography

Sources & evidence

ORD record
ord-abc91cf73c734c1ca30506cbe1aa245a
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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