Sodium Hydroxide → HCID 11474822, compound

HRID 1907830Notes

Reaction equation

HRID 1907830 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[O:10])[C:4]=2[CH:3]=[CH:2]1.[OH-].[Na+].Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH2:18][CH2:17]1.C(OCC)(=O)C.ClCCl>CS(C)=O>[Cl:29][C:24]1[CH:23]=[C:22]([N:19]2[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][N:1]3[C:9]4[CH2:8][CH2:7][CH2:6][C:5](=[O:10])[C:4]=4[CH:3]=[CH:2]3)[CH2:21][CH2:20]2)[CH:27]=[CH:26][C:25]=1[Cl:28]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneHCID 120698951-(2-Chloroethyl)-4-(3,4-dichlorophenyl)piperazineHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 11474822HCID 11474822, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 1,5,6,7-tetrahyroindol-4-one (107 mg) in DMSO (2 mL) was added powdered sodium hydroxide (33 mg) and the mixture was stirred at ambient temperature for 0.5 hours. 1-(2-Chloroethyl)-4-(3,4-dichlorophenyl)piperazine (220 mg) from step 1 was then added as a solution in DMSO (2 mL) and the resulting mixture stirred at ambient temperature for 24 hours then heated to approximately 60° C. for 2 hours, after which time thin layer chromatography (TLC) (ethyl acetate:dichloromethane 1:1) showed complete reaction. The reaction was poured into ice cold water (15 mL) and stirred for 0.5 hours. A solid mass formed and was separated by decanting the water. The aqueous layer was extracted with dichloromethane (10 mL). The solid mass was dissolved with dichloromethane (5 mL) and the combined organics were dried with sodium sulfate and the solvent removed under vacuum to obtain an oil (250 mg) as the titled compound.

Workup

  1. stirringthe resulting mixture stirred at ambient temperature for 24 hours
  2. temperaturethen heated to approximately 60° C. for 2 hours
  3. customreaction
  4. stirringstirred for 0.5 hours
  5. customA solid mass formed
  6. customwas separated
  7. customby decanting the water
  8. extractionThe aqueous layer was extracted with dichloromethane (10 mL)
  9. dissolutionThe solid mass was dissolved with dichloromethane (5 mL)
  10. dry with materialthe combined organics were dried with sodium sulfate
  11. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-de5a54aad2724978b502b39f4b5ea140
Source dataset
uspto-grants-2013_12
Patent number
US08598180B2

Reaction notes

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