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

HRID 1094580Notes

Reaction equation

HRID 1094580 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-cd56d8d64c474a99afa68116b165e828
Source dataset
uspto-grants-2012_03
Patent number
US08133992B2

Reaction notes

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