2,3-Dichloropyridine → Tert-butyl 4-(3-chloropyridin-2-yl)piperazine-1-carboxylate

HRID 1868009Notes

Reaction equation

HRID 1868009 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.Cl[C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][N:16]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:21][C:20]1[C:15]([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)=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 169882,3-DichloropyridineHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 11630777Tert-butyl 4-(3-chloropyridin-2-yl)piperazine-1-carboxylateYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-butyl piperazine-1-carboxylate (1.0 g, 5.37 mmol) and 2,3-dichloropyridine (795 mg, 5.37 mmol) charged to a microwave vial was added with diisopropylethylamine (2.34 mL, 13.42 mmol) and DMF (1.0 mL). The reaction mixture was subject to microwave irradiation at 165° C. for 30 minutes. The reaction was repeated six times in order to scale up. Combined reaction mixture was partitioned between EtOAc and water, organic layer washed with brine and dried over MgSO4. The crude product obtained by solvent evaporation was purified via flash column chromatography. tert-butyl 4-(3-chloropyridin-2-yl)piperazine-1-carboxylate was obtained in 20% yield (1.9 g) as yellow oil.

Workup

  1. customirradiation at 165° C. for 30 minutes
  2. customreaction mixture
  3. customwas partitioned between EtOAc and water, organic layer
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe crude product obtained by solvent evaporation
  7. customwas purified via flash column chromatography

Sources & evidence

ORD record
ord-8be30edf93144e5f8fedce5618504a51
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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