Morpholine → 4,5,6,7-tetrahydro-4-(2-(morpholin-4-yl)ethyl)-1-phenyl-1H-indazole

HRID 1943600Notes

Reaction equation

HRID 1943600 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][CH:16]=[CH:15][CH:14]=3)[N:7]=[CH:6][C:5]1=2.C([O-])([O-])=O.[K+].[K+].[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>CN(C=O)C.C(OCC)(=O)C>[N:25]1([CH2:2][CH2:3][CH:4]2[CH2:12][CH2:11][CH2:10][C:9]3[N:8]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:7]=[CH:6][C:5]2=3)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 23112897HCID 23112897, compound

Product 1

HCID 115314514,5,6,7-tetrahydro-4-(2-(morpholin-4-yl)ethyl)-1-phenyl-1H-indazoleYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(2-chloroethyl)-4,5,6,7-tetrahydro-1-phenyl-1H-indazole (423 mg, 1.62 mmol), K2CO3 (336 mg, 2.43 mmol), morpholin (0.42 mL, 4.87 mmol) and a catalytic amount of KI in 20 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 4,5,6,7-tetrahydro-4-(2-(morpholin-4-yl)ethyl)-1-phenyl-1H-indazole (384 mg, 1.23 mmol, 76%, 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-4445e1687aad4f539237c582704fc135
Source dataset
uspto-grants-2013_03
Patent number
US08394797B2

Reaction notes

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