Sodium Bicarbonate → 5-methoxy-3-[N-(4-(4-fluoro-phenyl)-4-oxo-butyl)piperidin-3-ylmethyl]-1-H-indole

HRID 356002Notes

Reaction equation

HRID 356002 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]1.C(=O)(O)[O-].[Na+].Cl[CH2:25][CH2:26][CH2:27][C:28]1([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)OCC[O:29]1>CN(C)C=O.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH2:25][CH2:26][CH2:27][C:28]([C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)=[O:29])[CH2:14]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27237782-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolaneHCID 189408255-methoxy-3-(piperidin-3-ylmethyl)-1H-indole

Product 1

HCID 189408725-methoxy-3-[N-(4-(4-fluoro-phenyl)-4-oxo-butyl)piperidin-3-ylmethyl]-1-H-indole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of compound of Description 6 [5-methoxy-3-(piperidin-3-ylmethyl)-1H-indole] (2 g; 0.0082 mol), sodium bicarbonate (0.68 g; 0.0082 mol), KI (0.087 g; 0.00053 mol) and 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane [2.2 g (1,8 ml); 0.009 mol] in dry dimethylformamide (25 ml) and tetrahydrofuran (25 ml), was heated under reflux for 5 hours. After evaporation under vacuum, the residue was flash chromatographed on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0.5) and the desired compound was obtained. A solution of the compound in ethanol was saturated with gaseous hydrogen chloride, a solid was precipitated. The title compound hydrochloride was collected by filtration.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customAfter evaporation under vacuum
  4. customchromatographed on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0.5)

Sources & evidence

ORD record
ord-8d8eec3188d9472e9532490aecf20030
Source dataset
uspto-grants-1998_11
Patent number
US05834493

Reaction notes

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