Hydrochloric Acid → HCID 314717, compound

HRID 1066784Notes

Reaction equation

HRID 1066784 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl.C=O.[C:11]([O-])(=O)C.[Na+].[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]1[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1>C(OCC)(=O)C>[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH2:11][N:5]2[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]2)=[C:18]1[CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 693814-MethylpiperidineHCID 517045Sodium AcetateHCID 211959852-[(4-Chlorophenoxy)methyl]-1-methyl-1H-indole

Product 1

HCID 314717HCID 314717, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere 4-methylpiperidine (0.109 ml, 0.09 g, 0.92 mmol), dissolved in 2.0 ml of ethyl acetate, was added to a round bottom flask which was then placed in an ice bath. Concentrated hydrochloric acid (0.084 ml) was then added and the reaction mixture was removed from the ice bath. To the reaction mixture were added formaldehyde (0.304 g, 1.01 mmol), sodium acetate (0.113 g, 1.38 mmol), and 1-methyl-2-(4-chlorophenoxymethyl)-1H-indole (0.250 g, 0.92 mmol). The resulting mixture was then heated to reflux and maintained at this temperature overnight. The progress of the reaction was monitored by thin layer chromatography.

Workup

  1. additionwas added to a round bottom flask which
  2. customwas then placed in an ice bath
  3. customthe reaction mixture was removed from the ice bath
  4. temperatureThe resulting mixture was then heated
  5. temperatureto reflux
  6. temperaturemaintained at this temperature overnight

Sources & evidence

ORD record
ord-c54c517730a2470e9ea808fc56c5b5cc
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

Loading…