Dichloromethane → HCID 58124027, compound

HRID 536633Notes

Reaction equation

HRID 536633 reaction equation
ClC(OC(Cl)C)=O.[CH3:8][C:9]12[CH2:23][CH:18]([N:19](C)[CH2:20][CH2:21]1)[CH2:17][CH2:16][C:15]1[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=1.C([O-])(O)=O.[Na+].ClCCl>ClCCCl>[CH3:8][C:9]12[CH2:23][CH:18]([NH:19][CH2:20][CH2:21]1)[CH2:17][CH2:16][C:15]1[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 5213051-Chloroethyl chloroformateHCID 12637767HCID 12637767, compound

Product 1

HCID 58124027HCID 58124027, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Chloroethyl chloroformate (3.8 mL) is added dropwise to a mixture of 1,11-dimethyl-11-aza-tricyclo[8.3.1.0*2,7*]tetradeca-2,4,6-triene (0.75 g) and NaHCO3 (2.9 g) in 1,2-dichloroethane (3.5 mL) chilled in an ice bath. The reaction mixture is warmed to room temperature in the cooling bath and stirred overnight. Then, dichloromethane (20 mL) is added and the precipitate is removed by filtration. The filtrate is concentrated under reduced pressure and the residue is dissolved in methanol (20 mL). The resulting solution is stirred at reflux temperature for 2 h. The solution is concentrated and the residue is purified by HPLC on reversed phase (water/MeCN/NH3) to give the title compound.

Workup

  1. temperaturechilled in an ice bath
  2. customthe precipitate is removed by filtration
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. dissolutionthe residue is dissolved in methanol (20 mL)
  5. stirringThe resulting solution is stirred
  6. temperatureat reflux temperature for 2 h
  7. concentrationThe solution is concentrated
  8. customthe residue is purified by HPLC on reversed phase (water/MeCN/NH3)

Sources & evidence

ORD record
ord-e81db5562bfb48c4b754287473ceb7c2
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

Loading…