Ethanol → HCID 57276823, compound

HRID 481671Notes

Reaction equation

HRID 481671 reaction equation
C(O)C.[Cl:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH:19]=3)=[CH:10][NH:11]2)=[CH:7][CH:6]=1.[O:20]1[CH2:22][C@H:21]1[CH2:23][O:24][C:25]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:26]=1[CH:27]=[CH:28][NH:29]2>CS(C)=O>[Cl:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:14]3[CH2:15][CH2:16][N:17]([CH2:22][C@H:21]([OH:20])[CH2:23][O:24][C:25]4[CH:33]=[CH:32][CH:31]=[C:30]5[C:26]=4[CH:27]=[CH:28][NH:29]5)[CH2:18][CH:19]=3)=[CH:10][NH:11]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 100598546-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 10943254(2s)-Glycidyl indol-4-yl ether

Product 1

HCID 57276823HCID 57276823, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 5 mL of dry ethanol were added 6-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (1.54 g, 6.61 mmol) and (S)-(+)-4-(oxiranylmethoxy)-1H-indole (1.25 g, 6.61 mmol). The mixture was heated at the reflux temperature for about 6 hours, and was then cooled and concentrated. The residue was purified by silica gel chromatography with 95/5 chloroform/methanol. The product was isolated as a yellow foam. Yield 1.52 g (55%). mp 200°-202° C. FDMS m/e=421 (M+ of free base). α[D]589 =+4.39 (c=1.00, dimethylsulfoxide)

Workup

  1. temperatureThe mixture was heated at the reflux temperature for about 6 hours
  2. temperaturewas then cooled
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography with 95/5 chloroform/methanol
  5. customThe product was isolated as a yellow foam

Sources & evidence

ORD record
ord-0215226201cd4783874360ccccd951cd
Source dataset
uspto-grants-1998_08
Patent number
US05789402

Reaction notes

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