1-Bromo-2-Chloroethane → HCID 11098035, compound

HRID 1771191Notes

Reaction equation

HRID 1771191 reaction equation
[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][Cl:26]>C(#N)C>[Cl:26][CH2:25][CH2:24][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 11098035HCID 11098035, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl piperazine-1-carboxylate (1.00 g, 4.54 mmol) and K2CO3 (1.255 g, 9.08 mmol) were dissolved in acetonitrile (12.87 ml) to form a suspension. 1-bromo-2-chloroethane (2.3 ml, 27.24 mmol) was added to the reaction mixture at r.t and the resulting mixture was stirred at this temperature for 96 hours. The reaction mixture was filtered, and the filtrate concentrated under reduced pressure. Purification by column chromatography (ISCO, silica gel column, eluting with 0→100% EtOAc in hexanes) gave the title compound (0.64 g, yield: 50%).

Workup

  1. customto form a suspension
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customPurification
  5. washby column chromatography (ISCO, silica gel column, eluting with 0→100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4e1bbec0c2954f7dae0cf99baf12c034
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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