Triethylamine → Tert-butyl 4-(5-chloropyridin-2-yl)piperazine-1-carboxylate

HRID 509268Notes

Reaction equation

HRID 509268 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.Br[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1.C(N(CC)CC)C>C(#N)C>[Cl:21][C:18]1[CH:19]=[CH:20][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]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 8170982-Bromo-5-chloropyridine

Product 1

HCID 57550329Tert-butyl 4-(5-chloropyridin-2-yl)piperazine-1-carboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tert-butyl piperazine-1-carboxylate (300 mg, 1.611 mmol) and 2-bromo-5-chloropyridine (465 mg, 2.416 mmol) were dissolved in acetonitrile (3 ml), followed by addition of triethylamine (0.45 ml, 3.222 mmol), and then the resulting liquid was subjected to microwave irradiation at 150° C. for 2 hours. The resulting reaction liquid was concentrated under reduced pressure, followed by addition of a saturated aqueous ammonium chloride solution (10 ml), and extracted with MC (15 ml×2). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (20% EtOAc/Hexanes), to obtain 177 mg of colorless oil (37%).

Workup

  1. customirradiation at 150° C. for 2 hours
  2. customThe resulting reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. additionfollowed by addition of a saturated aqueous ammonium chloride solution (10 ml)
  5. extractionextracted with MC (15 ml×2)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfollowed by filtration and concentration
  8. customthe residue thus obtained

Sources & evidence

ORD record
ord-3e7658f9d8514c838ddaf2623d70b353
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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