Methyl iodide → (6-benzyloxy-1H-indol-3-ylmethyl)-trimethylammonium iodide

HRID 37941Notes

Reaction equation

HRID 37941 reaction equation
[CH3:1][I:2].[CH3:3][N:4]([CH2:6][C:7]1[C:11]2[CH:12]=[CH:13][C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][C:10]=2[NH:9][CH:8]=1)[CH3:5]>C1C=CC=CC=1>[I-:2].[CH2:17]([O:16][C:14]1[CH:15]=[C:10]2[C:11]([C:7]([CH2:6][N+:4]([CH3:1])([CH3:3])[CH3:5])=[CH:8][NH:9]2)=[CH:12][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 2608086-Benzyloxygramine

Product 1

HCID 86590995(6-benzyloxy-1H-indol-3-ylmethyl)-trimethylammonium iodide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Methyl iodide (15 mL) was added to a stirred mixture of 6-benzyloxygramine (10 g, 35.66 mmol) in dry benzene (150 mL) at ambient temperature. The mixture was stirred at ambient temperature for 30 minutes, then allowed to stand in the dark overnight. The solid was collected by filtration, then dried in high vacuum to give (6-benzyloxy-1H-indol-3-ylmethyl)trimethylammonium iodide (17.5 g).

Workup

  1. customto stand in the dark overnight
  2. filtrationThe solid was collected by filtration
  3. customdried in high vacuum

Sources & evidence

ORD record
ord-c1828833780247f2a4f12f4f8c12f980
Source dataset
uspto-grants-2013_09
Patent number
US08524704B2

Reaction notes

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