Triethylamine → t-Butyl 4-(4-methoxycarbonylbenzoyl)piperazine-1-carboxylate

HRID 747682Notes

Reaction equation

HRID 747682 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl-].[C:22]([O:33][CH3:34])(=[O:32])[C:23]1[CH:31]=[CH:30][C:26]([C:27]([O-])=[O:28])=[CH:25][CH:24]=1>CN(C)C=O.Cl>[CH3:34][O:33][C:22]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[O:28])=[CH:25][CH:24]=1)=[O:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 22493623Monomethyl terephthalate chloride

Product 1

HCID 17789205t-Butyl 4-(4-methoxycarbonylbenzoyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

4.93 g (26.5 mmol) of t-butyl piperazine-1-carboxylate and 4.8 ml (34.5 mmol) of triethylamine were stirred in 50 ml of dimethylformamide under cooling with ice. 5.25 g (26.5 mmol) of monomethyl terephthalate chloride was slowly added to the resultant mixture, and they were stirred for 16 hours. The temperature was elevated to room temperature, and the reaction liquid was diluted with 1 N hydrochloric acid. After the extraction with ethyl acetate followed by the treatment in an ordinary manner, the title compound was obtained.

Workup

  1. temperatureunder cooling with ice
  2. customwas elevated to room temperature
  3. customthe reaction liquid
  4. extractionAfter the extraction with ethyl acetate

Sources & evidence

ORD record
ord-f920af3f16aa4415b543e2effaf1a3a1
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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