Ethyl Bromide → HCID 20537465, compound

HRID 1155695Notes

Reaction equation

HRID 1155695 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[C:6]([C:11]3([OH:17])[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:24](Br)[CH3:25]>CN(C)C=O.O>[CH2:24]([N:13]1[CH2:14][CH2:15][CH2:16][C:11]([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH:4]=[CH:3][NH:2]3)([OH:17])[CH2:12]1)[CH3:25]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 10340Sodium CarbonateHCID 12900686HCID 12900686, compound

Product 1

HCID 20537465HCID 20537465, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 10 g of 3-(1H-indol-4-yl)-3-piperidinol hydrochloride in 200 ml of dimethylformamide was agitated for 4 hours under an inert atmosphere with 13.44 g of sodium carbonate and 4.2 ml of ethyl bromide. The mixture was taken up in water and was extracted with ethyl acetate. The organic phase was washed with water, dried, filtered and evaporated to dryness under reduced pressure at 50° C. The residue was purified by chromatography over silica and eluted with a 6-3-1 mixture of cyclohexane-chloroform-triethylamine to obtain 6.6 g of 1-ethyl-3-(1H-indol-4-yl)-3-piperidinol which was used as is for the following step.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure at 50° C
  6. customThe residue was purified by chromatography over silica
  7. washeluted with a 6-3-1 mixture of cyclohexane-chloroform-triethylamine

Sources & evidence

ORD record
ord-095436143ccf47efa670d306dab120ff
Source dataset
uspto-grants-1982_06
Patent number
US04332808

Reaction notes

Loading…