Ethanol → (2S)-(+)-3-[4-(5-chloro-3-indolyl)piperidin-1-yl]-1-(4-indolyloxy)-2-propanol

HRID 1779634Notes

Reaction equation

HRID 1779634 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(O)C>CS(C)=O>[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[CH:25]1[CH2:30][CH2:29][N:28]([CH2:3][C@H:2]([OH:1])[CH2:4][O:5][C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[CH:8]=[CH:9][NH:10]3)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 702EthanolHCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 128313754-(5-chloro-[1H]-indol-3-yl)-piperidine

Product 1

HCID 70218438(2S)-(+)-3-[4-(5-chloro-3-indolyl)piperidin-1-yl]-1-(4-indolyloxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in a fashion similar to that described in Example 1 using (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 5-chloro-3-(piperidin-4-yl)-1H-indole using ethanol as the reaction solvent. Yield 0.380 g (42%) as a yellowish foam. mp 109°-114° C. (dec) FDMS m/e=423 (M+ of free base). α[D]589 =+6.5 (c=1.04, dimethylsulfoxide).

Sources & evidence

ORD record
ord-947868b5f9b946a8ad05b9a18628e389
Source dataset
uspto-grants-1997_05
Patent number
US05627196

Reaction notes

Loading…