Chlorine → HCID 18656670, compound

HRID 1289900Notes

Reaction equation

HRID 1289900 reaction equation
[O:1]1[C:5]([C:6]2[CH:14]=[CH:13][C:12]3[NH:11][CH2:10][C@@H:9]4[CH2:15][C@H:16]([N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH2:17][C:7]=2[C:8]=34)=[CH:4][CH:3]=[N:2]1.ClCl>O=[Mn]=O>[O:1]1[C:5]([C:6]2[CH:14]=[CH:13][C:12]3[NH:11][CH:10]=[C:9]4[CH2:15][C@H:16]([N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH2:17][C:7]=2[C:8]=34)=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 15221118HCID 15221118, compound

Product 1

HCID 18656670HCID 18656670, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

A mixture of (-)(2aR,4S)-6-(5-isoxazolyl)-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (253 mg, 0.8 mmol) and 1 g of MnO2 in 100 ml of CH2 Cl2 was sonicated at 50-55 KHz for four hours. The reaction mixture was warmed to reflux during the time period. After four hours, the reaction mixture was filtered through a celite pad and the filtrate was concentrated to dryness in vacuo. The resulting residue was chromatographed (flash column, silica gel, EtOAc) to provide 130 mg of title product. Recrystallization from hexane gave 60 mg of purified title product.

Workup

  1. customwas sonicated at 50-55 KHz for four hours
  2. temperatureThe reaction mixture was warmed
  3. temperatureto reflux during the time period
  4. filtrationthe reaction mixture was filtered through a celite pad
  5. concentrationthe filtrate was concentrated to dryness in vacuo
  6. customThe resulting residue was chromatographed (flash column, silica gel, EtOAc)

Sources & evidence

ORD record
ord-2c52ef88b3f442e09ace80c00a72eff4
Source dataset
uspto-grants-1998_05
Patent number
US05750554

Reaction notes

Loading…