Benzyl Bromide → 1-benzyl-5-methoxy-7-methyl-3-(1-methylpiperdin-4-yl)-1H-indole

HRID 1766236Notes

Reaction equation

HRID 1766236 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.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[H-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[CH2:20]([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)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 2855718-Crown-6HCID 82127Potassium hydrideHCID 179800985-methoxy-7-methyl-3-(1-methylpiperidin-4-yl)-1H-indole

Product 1

HCID 694313131-benzyl-5-methoxy-7-methyl-3-(1-methylpiperdin-4-yl)-1H-indoleYield 81%

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 mmol, 1.50 g) and benzyl bromide (5.81 mmol, 0.993 g), THF (100 mL), 35% potassium hydride (5.81 mmol, 0.665 g), and 18-crown-6 (0.58 mmol, 0.153 g) afforded 1.63 g (81%) of the title compound: mass spectrum (ion spray): m/z=349 (M+1): Calculated for C23H28N2O-0.3H2O: C, 78.06; H, 8.15; N, 7.92. Found: C, 78.13; H, 7.84; N, 8.03.

Workup

  1. customBy a method similar to Preparation 26

Sources & evidence

ORD record
ord-a481575b9b664064af56f4c177c298f8
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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