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

HRID 1176244

Reaction equation

HRID 1176244 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-a65d1414143b400d8ae063974715836b
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Linked notes

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