Terephthaloyl chloride → HCID 66917476, compound

HRID 1881715Notes

Reaction equation

HRID 1881715 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C([NH:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(OC(C)(C)C)=O>CN(C=O)C>[NH2:20][CH:21]1[CH2:26][CH2:25][N:24]([C:1]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([N:24]3[CH2:23][CH2:22][CH:21]([NH2:20])[CH2:26][CH2:25]3)=[O:7])=[CH:4][CH:3]=2)=[O:11])[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 7488Terephthaloyl chlorideHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 66917476HCID 66917476, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of terephthaloyl chloride (1.02 g, 5.0 mmol) in DMF (10 mL) under an inert atmosphere of argon is treated dropwise with a solution of 4-(N-Boc-amino)piperidine (2.00 g, 10.0 mmol) over 20 minutes. The reaction mixture is allowed to stir at room temperature for 40 minutes and then TEA (2.09 mL, 15.0 mmol) is added dropwise. A white suspension forms and stirring continues for 2 hours. The resulting mixture is washed with saturated NaHCO3 solution (50 mL) and water (100 mL). The resulting mixture is filtered under vacuum using phase separating paper to afford a white solid. The solid is dried under vacuum at 45° C. to yield the required product. [M+H]+ 531

Workup

  1. stirringA white suspension forms and stirring
  2. waitcontinues for 2 hours
  3. washThe resulting mixture is washed with saturated NaHCO3 solution (50 mL) and water (100 mL)
  4. filtrationThe resulting mixture is filtered under vacuum
  5. customseparating paper
  6. customto afford a white solid
  7. customThe solid is dried under vacuum at 45° C.

Sources & evidence

ORD record
ord-1205d959aa2b4c7daa08e50467c2ce54
Source dataset
uspto-grants-2012_11
Patent number
US08318935B2

Reaction notes

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