Diisopropylethylamine → Ethyl 6-[1-(tert-butoxycarbonyl)piperazin-4-yl]-5-chloronicotinate

HRID 1444099Notes

Reaction equation

HRID 1444099 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([Cl:11])[C:8](Cl)=[N:7][CH:6]=1)[CH3:2].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].CCN(C(C)C)C(C)C>CC(N(C)C)=O>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:8]2[C:9]([Cl:11])=[CH:10][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:13])=[CH:6][N:7]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 16762519Ethyl 5,6-Dichloronicotinate

Product 1

HCID 59168365Ethyl 6-[1-(tert-butoxycarbonyl)piperazin-4-yl]-5-chloronicotinate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Heat a solution of 5,6-dichloro-nicotinic acid ethyl ester (TCI America) (4.43 g, 0.02 mol), piperazine-1-carboxylic acid tert-butyl ester (4.13 g, 0.022 mol) and DIEA (5.2 mL, 0.03 mol) in DMA at 110° C. for 5 h. Partition the reaction mixture between water and EtOAc. Wash the EtOAc layer with water (1×) and brine (1×), dry (Na2SO4) and concentrate under reduced pressure to give the title compound as an orange oil.

Workup

  1. customPartition the reaction mixture between water and EtOAc
  2. washWash the EtOAc layer with water (1×) and brine (1×)
  3. dry with materialdry (Na2SO4)
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-cc0e2e35daa345449c0bdfa81c50ac47
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

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