Diisopropylethylamine → 1,1-Dimethylethyl 4-[(4-chloro-2-pyridinyl)carbonyl]-1-piperazinecarboxylate

HRID 912299Notes

Reaction equation

HRID 912299 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.C(N(C(C)C)C(C)C)C.[C:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>ClCCl>[C:23]([O:22][C:20]([N:27]1[CH2:32][CH2:31][N:30]([C:8]([C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=2)=[O:9])[CH2:29][CH2:28]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 110951464-chloropyridine-2-carbonyl Chloride

Product 1

HCID 592442111,1-Dimethylethyl 4-[(4-chloro-2-pyridinyl)carbonyl]-1-piperazinecarboxylateYield 51.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (4 ml) of 4-chloropicolinic acid chloride (175 mg, 0.994 mmol), N-ethyldiisopropylamine (346 μl, 1.99 mol) and N-Boc-piperazine (278 mg, 1.49 mmol) were added, followed by stirring at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane/methanol=60/1), to obtain 4-(4-chloro-pyridine-2-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester (166 mg, 51%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (dichloromethane/methanol=60/1)

Sources & evidence

ORD record
ord-e7890efdcc8948f3aeaa436eac074aa8
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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