Triethylamine → Benzyl 4-(5-benzoylpyrimidin-2-yl)piperazine-1-carboxylate

HRID 522688Notes

Reaction equation

HRID 522688 reaction equation
[C:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[N:13][CH:14]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>ClCCl>[C:7]([C:9]1[CH:14]=[N:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:30])[CH2:17][CH2:16]2)=[N:11][CH:10]=1)(=[O:8])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 118022471Phenyl(2-(piperazin-1-yl)pyrimidin-5-yl)methanone

Product 1

HCID 118022147Benzyl 4-(5-benzoylpyrimidin-2-yl)piperazine-1-carboxylateYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of phenyl(2-(piperazin-1-yl)pyrimidin-5-yl)methanone (crude, 2.6 mmol assumed) and triethylamine (780 mg, 7.8 mmol) in dichloromethane (10 mL) was added benzyl chloroformate (663 mg, 3.9 mmol). The reaction mixture was stirred at room temperature for 2 hours, and diluted with dichloromethane (100 mL). The organic phase was washed with water (100 mL) and brine (50 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (etroleum ether/ethyl acetate=4:1˜2:1) to give benzyl 4-(5-benzoylpyrimidin-2-yl)piperazine-1-carboxylate (600 mg, 57%) as a yellow solid. MS (ES+) C23H22N4O3 requires: 402, found: 403 [M+H]+.

Workup

  1. washThe organic phase was washed with water (100 mL) and brine (50 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (etroleum ether/ethyl acetate=4:1˜2:1)

Sources & evidence

ORD record
ord-4d0884d1dd4246d8955318c986ff4598
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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