Chlorine → HCID 15227862, compound

HRID 1488538Notes

Reaction equation

HRID 1488538 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([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)=[N:2]1.ClCl>O=[Mn]=O>[O:1]1[CH:5]=[CH:4][C:3]([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)=[N:2]1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 18654737HCID 18654737, compound

Product 1

HCID 15227862HCID 15227862, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

A mixture of (-)(2aR,4S)-6-(3-isoxazolyl)-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (400 mg, 1.2 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 55 mg of title product as an oil. MS m/e 323(FD) NMR (300 MHz, CDCl3) δ 0.90 (t, 6H); 1.2-1.6 (m, 5H); 2.2-3.6 (m, 8H); 6.6 (s, 1H); 6.9 (s, 1H); 7.2 (d, 1H); 7.4 (d, 1H); 8.0 (bs, 1H); 8.4 (s, 1H).

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-663fd5b5c9994bd0bc621b9633cdb577
Source dataset
uspto-grants-1997_10
Patent number
US05674884

Reaction notes

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