Hydrochloric Acid → HCID 21196019, compound

HRID 1066785Notes

Reaction equation

HRID 1066785 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:5][CH:6]=1.Cl.C=O.[C:16]([O-])(=O)C.[Na+].[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[C:23]1[CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1>ClC(Cl)C>[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH2:16][N:10]2[CH2:9][CH2:8][N:7]([C:4]3[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=3)[CH2:12][CH2:11]2)=[C:23]1[CH2:31][O:32][C:33]1[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 70961-PhenylpiperazineHCID 517045Sodium AcetateHCID 211959852-[(4-Chlorophenoxy)methyl]-1-methyl-1H-indole

Product 1

HCID 21196019HCID 21196019, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Under a nitrogen atmosphere in a round bottom flask, phenylpiperazine (0.149 g, 0.920 mmol) was dissolved in 2.0 ml of dichloroethane. The reaction vessel was placed in an ice bath. Concentrated hydrochloric acid (0.084 ml, 1.01 mmol) was added and the reaction vessel was removed from the ice bath. Paraformaldehyde (0.304 g, 1.01 mmol) and sodium acetate (0.113 g, 0.920 mmol) were then added, followed by the addition of 1-methyl-2-(4-chlorophenoxymethyl)-1H-indole (0.250 g, 0.920 mmol). The reaction mixture was then heated to reflux and maintained at this temperature for about six hours. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was then stirred at room temperature for about three days.

Workup

  1. customThe reaction vessel was placed in an ice bath
  2. customthe reaction vessel was removed from the ice bath
  3. temperatureThe reaction mixture was then heated
  4. temperatureto reflux
  5. temperaturemaintained at this temperature for about six hours

Sources & evidence

ORD record
ord-6678a9b39e1e4c73a2b4d519bac6bd2d
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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