Potassium Carbonate → 1-Boc-4-(2-chloropyridin-4-ylmethyl)piperazine

HRID 1257107Notes

Reaction equation

HRID 1257107 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8]Cl)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CN(C=O)C>[C:16]([N:23]1[CH2:24][CH2:25][N:26]([CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)[CH2:27][CH2:28]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 111265732-Chloro-4-(chloromethyl)pyridine

Product 1

HCID 866538601-Boc-4-(2-chloropyridin-4-ylmethyl)piperazineYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-chloro-4-(chloromethyl)pyridine (500 mg, 2.05 mmol) and K2CO3 (1.14 g, 4 equiv) in DMF (50 ml), was added N-Boc-piperazine (558 mg, 1.1 equiv.). The mixture was stirred at rt for 1 h, after which TLC showed that no starting materials remained. The DMF was removed under vacuum and the residue was partitioned between water and ethyl acetate. The organic layer was collected, dried over anhydrous Na2SO4, concentrated, and applied onto a silica gel column. The title compound (570 mg, yield 91%) was obtained as a colorless gel.

Workup

  1. customThe DMF was removed under vacuum
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic layer was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0fa768356b594268a1f5af046b2067c9
Source dataset
uspto-grants-2013_06
Patent number
US08461339B2

Reaction notes

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