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

HRID 2195032Notes

Reaction equation

HRID 2195032 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-94d26ee773dc4331b24c008d2f2f81a8
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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