HCID 23505589, compound → 1-(4-Hydroxybenzyl)-2-(methylaminomethyl)indole

HRID 1884524Notes

Reaction equation

HRID 1884524 reaction equation
C([O:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[C:15]2[CH2:23][NH:24][CH3:25])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[C:15]2[CH2:23][NH:24][CH3:25])=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 23505589HCID 23505589, compound

Product 1

HCID 235055811-(4-Hydroxybenzyl)-2-(methylaminomethyl)indoleYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(4-benzyloxybenzyl)-2-(methylaminomethyl)indole (27.1 g, 75.9 mmole) in methanol (75 mL) at RT in a Parr hydrogenation flask was added 10% Pd/C (0.5 g). The reaction mixture was shaken under 45 psi of H2 for 4 hr. The suspension was filtered through celite®, and the filter pad was washed with methanol. The filtrate was concentrated on the rotavap, and the residue was dried under high vacuum to afford the titled compound (18.0 g, 89%) as an off-white solid: MS (ES) m/e 268 (M+H)+.

Workup

  1. filtrationThe suspension was filtered through celite®
  2. washthe filter pad was washed with methanol
  3. concentrationThe filtrate was concentrated on the rotavap
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-6b72284aa6924adeb5bf3b6dc5ca9eba
Source dataset
uspto-grants-2004_07
Patent number
US06765005B2

Reaction notes

Loading…