Potassium Carbonate → HCID 11554272, compound

HRID 1943606Notes

Reaction equation

HRID 1943606 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[CH2:12][CH2:11][CH2:10][C:9]2[N:8]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=3)[N:7]=[CH:6][C:5]1=2.C([O-])([O-])=O.[K+].[K+].[C:27]1([CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:20][C:15]1[CH:14]=[C:13]([N:8]2[C:9]3[CH2:10][CH2:11][CH2:12][CH:4]([CH2:3][CH2:2][N:36]4[CH2:37][CH2:38][CH:33]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH2:34][CH2:35]4)[C:5]=3[CH:6]=[N:7]2)[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 23112900HCID 23112900, compound

Product 1

HCID 11554272HCID 11554272, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(2-chloroethyl)-4,5,6,7-tetrahydro-1-(3,4-dichlorophenyl)-1H-indazole (235 mg, 0.71 mmol), K2CO3 (99 mg, 0.71 mmol), 4-phenylpiperidine (97 mg, 0.71 mmol) and a catalytic amount of KI in 5 mL of DMF is heated to reflux during 18 hours. The solvent is eliminated at reduced pressure, the crude is diluted with ethyl acetate, washed with water, and the organic phase is evaporated at reduced pressure. The resultant crude is purified by chromatography on silica-gel to obtain 1-(3,4-dichlorophenyl)-4,5,6,7-tetrahydro-4-(2-(4-phenylpiperidin-1-yl)ethyl)-1H-indazole (146 mg, 0.32 mmol, 45%, oil).

Workup

  1. temperatureto reflux during 18 hours
  2. washwashed with water
  3. customthe organic phase is evaporated at reduced pressure
  4. customThe resultant crude is purified by chromatography on silica-gel

Sources & evidence

ORD record
ord-1dd265e89b8b4b429edf9402df7b2575
Source dataset
uspto-grants-2013_03
Patent number
US08394797B2

Reaction notes

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