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

HRID 736077Notes

Reaction equation

HRID 736077 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 vaccum 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 vaccum

Sources & evidence

ORD record
ord-4ece5798f78d424a97f5aa3fc31e895b
Source dataset
uspto-grants-2009_09
Patent number
US07595311B2

Reaction notes

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