18-Crown-6 → 1-propyl-5-methoxy-7-methyl-3-(1-methylpiperdin-4-yl)-1H-indole

HRID 1766237Notes

Reaction equation

HRID 1766237 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1.I[CH2:21][CH2:22][CH3:23].[H-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[CH2:21]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][C:10]=2[CH3:12])[C:6]([CH:13]2[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]2)=[CH:7]1)[CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 336431-IodopropaneHCID 82127Potassium hydrideHCID 179800985-methoxy-7-methyl-3-(1-methylpiperidin-4-yl)-1H-indole

Product 1

HCID 694324431-propyl-5-methoxy-7-methyl-3-(1-methylpiperdin-4-yl)-1H-indoleYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By a method similar to Preparation 26, using 5-methoxy-7-methyl-3-(1-methylpiperidin-4-yl)-1H-indole (5.81 mmole, 1.50 g), iodopropane (5.81 mmole, 0.987 g, 0.566 mL) in THF (100 mL), potassium hydride (5.81 mmole, 0.665 g), and 18-crown-6 (0.58 mmole, 0.153 g) afforded 1.26 g (72%) of the title compound: mass spectrum (ion spray): m/z=301 (M+1);. Calculated for C19H28N2O-0.3H2O: C, 74.61; H, 9.43; N, 9.16. Found: C, 74.37; H, 9.03; N, 9.01.

Workup

  1. customBy a method similar to Preparation 26

Sources & evidence

ORD record
ord-f4865c3991f846668e0be014472b903d
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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