Ethanol → (2S)-(+)-3-[4-(7-chloro-3-indolyl)piperidin-1-yl]-1-(4-indolyloxy)-2-propanol

HRID 565522Notes

Reaction equation

HRID 565522 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]=[CH:18][CH:19]=[C:20]2[C:24]=1[NH:23][CH:22]=[C:21]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]=[CH:18][CH:19]=[C:20]2[C:24]=1[NH:23][CH:22]=[C:21]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 120720367-chloro-3-(piperidin-4-yl)-1H-indole

Product 1

HCID 57102677(2S)-(+)-3-[4-(7-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 (0.406 g, 2.13 mmol) and 7-chloro-3-(piperidin-4-yl)-1H-indole (0.500 g, 2.13 mmol) using ethanol as reaction solvent. Yield 0.325 g (35%) as a colorless powder. mp 186-189° C. FDMS m/e=423 (M+ of free base). α[D]589=+8.44 (c=1.09, dimethylsulfoxide).

Workup

  1. customas reaction solvent

Sources & evidence

ORD record
ord-24f0350170934e7e9426ecf3a901857b
Source dataset
uspto-grants-2001_01
Patent number
US06172073B2

Reaction notes

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