Sodium Carbonate → HCID 20537493, compound

HRID 1155686Notes

Reaction equation

HRID 1155686 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7](I)[CH2:8][CH3:9].Cl.[CH3:12][N:13]1[C:21]2[C:16](=[C:17]([C:22]3([OH:28])[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]3)[CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1>CN(C)C=O.O>[CH2:7]([N:24]1[CH2:25][CH2:26][CH2:27][C:22]([C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:16]=2[CH:15]=[CH:14][N:13]3[CH3:12])([OH:28])[CH2:23]1)[CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 336431-IodopropaneHCID 20537466HCID 20537466, compound

Product 1

HCID 20537493HCID 20537493, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

14.5 g of sodium carbonate and 6 ml of propyl iodide were added to a mixture of 12 g of 3-(1-methyl-1H-indol-4-yl)-3-piperidinol hydrochloride in 240 ml of dimethylformamide and the mixture was stirred for 20 hours and then was diluted with water. The mixture was extracted with ethyl acetate and the organic phase was washed with aqueous sodium chloride solution, dried and evaporated to dryness under reduced pressure. The 11 g of residue were chromtographed over silica gel and eluted with a 9-1 cyclohexane-triethylamine mixture to obtain 8.2 g of 1-propyl-3-(1-methyl-1H-indol-4-yl)-3-piperidinol) with an Rf=0.2.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic phase was washed with aqueous sodium chloride solution
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. washeluted with a 9-1 cyclohexane-triethylamine mixture

Sources & evidence

ORD record
ord-10fb00040dfe4e4daf07400e28324138
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Reaction notes

Loading…