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

HRID 1180514Notes

Reaction equation

HRID 1180514 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 K1 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-24468d837b2745759c46b7a4fe674e41
Source dataset
uspto-grants-2007_10
Patent number
US07282499B2

Reaction notes

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