Triethylamine → 6-(4-{4-[3-(2-Methoxybenzyloxy)propoxy]phenyl}piperidin-3-yloxymethyl)-1-(3-methoxypropyl)-3-methyl-1H-indole

HRID 1712276Notes

Reaction equation

HRID 1712276 reaction equation
Br[C:2]1[C:3]([CH2:17][O:18][CH:19]2[CH:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[O:43][CH3:44])=[CH:27][CH:26]=3)[CH2:23][CH2:22][N:21](C(OCC3C=CC=CC=3)=O)[CH2:20]2)=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:8]=[C:7]2[CH3:16].C(N(CC)CC)C>CO.[Pd]>[CH3:44][O:43][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[CH2:36][O:35][CH2:34][CH2:33][CH2:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([CH:24]2[CH2:23][CH2:22][NH:21][CH2:20][CH:19]2[O:18][CH2:17][C:3]2[CH:2]=[C:10]3[C:6]([C:7]([CH3:16])=[CH:8][N:9]3[CH2:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:5][CH:4]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 68501531Benzyl 3-[7-bromo-1-(3-methoxypropyl)-3-methyl-1H-indol-6-yl methoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Product 1

HCID 118583506-(4-{4-[3-(2-Methoxybenzyloxy)propoxy]phenyl}piperidin-3-yloxymethyl)-1-(3-methoxypropyl)-3-methyl-1H-indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The solution of 0.150 g of benzyl 3-[7-bromo-1-(3-methoxypropyl)-3-methyl-1H-indol-6-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 5.0 ml of methanol is admixed with 0.027 ml of triethylamine and hydrogenated in the presence of 30 mg of 5% Pd/C at room temperature over 16 hours. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. filtrationThe reaction mixture is clarified by filtration
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-cff7f9822f8a4be9986200b575ca3b20
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

Loading…