Potassium Carbonate → 3-[4-(5-Chloro-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-indolyloxy)propane

HRID 565546Notes

Reaction equation

HRID 565546 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1.Cl[CH2:18][CH2:19][CH2:20][O:21][C:22]1[C:23]2[CH:24]=[CH:25][NH:26][C:27]=2[CH:28]=[CH:29][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][N:14]([CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:23]=2[CH:24]=[CH:25][NH:26]3)[CH2:15][CH:16]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 116941694-(3-chloropropoxy)-1H-indole

Product 1

HCID 212682983-[4-(5-Chloro-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-indolyloxy)propane

Procedure

The title compound was prepared in a fashion similar to that described in Example 192 from 5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.50 g, 2.2 mmol), 1-chloro-3-(1H-indole-4-oxy)propane (0.45 g, 2.2 mmol) and potassium carbonate (0.35 g, 2.5 mmol). The product was isolated as a white foam. Yield 220 mg (25%). mp 198-202° C. FDMS m/e=406 (M+ of free base).

Workup

  1. customThe product was isolated as a white foam

Sources & evidence

ORD record
ord-3e611651bb3f4c12b137fdf815233509
Source dataset
uspto-grants-2001_01
Patent number
US06172073B2

Reaction notes

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