HCID 21108202, compound → HCID 21108382, compound

HRID 1766007Notes

Reaction equation

HRID 1766007 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH:13](O)[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=O)C>Cl>[NH:4]1[C:12]2[C:7](=[CH:8][C:9](/[CH:13]=[CH:14]/[CH2:15][N:16]([CH3:18])[CH3:17])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

3

Reactant 1

HCID 21108202HCID 21108202, compound

Product 1

HCID 21108382HCID 21108382, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 3-[1-acetyl-2,3-dihydro-1H-indol-5-yl]-3-hydroxy-N,N-dimethyl-1-propanamine (3.3 g) obtained in 1) above and concd. hydrochloric acid (20 ml) was heated for 16 hours under reflux. The reaction solution was cooled to room temperature, then concentrated under reduced pressure, diluted with water, made basic with 2 N aqueous sodium hydroxide and extracted with ethyl acetate. The extract was washed with a saturated saline solution and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure, whereby the title compound (2.3 g) was obtained as oily matter.

Workup

  1. customobtained in 1) above and concd
  2. temperatureunder reflux
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with a saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled away under reduced pressure, whereby the title compound (2.3 g)
  9. customwas obtained as oily matter

Sources & evidence

ORD record
ord-30a2e3291e6c4eb49aec0fc8f1afc66a
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

Loading…