Morpholine → HCID 11681118, compound

HRID 1943611Notes

Reaction equation

HRID 1943611 reaction equation
C1(C)C=CC(S([O-])(=O)=[O:8])=CC=1.[C:12]1([N:18]2[C:26]3[CH2:25][CH2:24][CH2:23][C:22](=[CH:27][CH2:28][N+:29]4[CH:34]=[CH:33]C=[CH:31][CH:30]=4)[C:21]=3[CH:20]=[N:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1CCOCC1>C(#N)C.C(OCC)(=O)C>[N:29]1([CH2:28]/[CH:27]=[C:22]2/[C:21]3[CH:20]=[N:19][N:18]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:26]=3[CH2:25][CH2:24][CH2:23]/2)[CH2:34][CH2:33][O:8][CH2:31][CH2:30]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 74017985HCID 74017985, compound

Product 1

HCID 11681118HCID 11681118, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[2-(1-phenyl-1,5,6,7-tetrahydro-indazol-4-ylidene)-ethyl]-pyridinium toluene-4-sulfonate (290 mg, 0.63 mmol) and morpholin (180 mg, 1.5 mmol) in 15 mL of acetonitrile is refluxed during 4 hours, following the reaction by TLC. The solvent is next evaporated, the crude is diluted in ethyl acetate and washed three times with water. Then the organic phase is evaporated under reduced pressure. The crude thus obtained is purified by silica gel chromatography giving (E)-4,5,6,7-tetrahydro-4-(2-(morpholin-4-yl)ethylidene)-1-phenyl-1H-indazole (110 mg, 0.36 mmol, 57%, beige solid, m.p=114-116° C.).

Workup

  1. temperatureis refluxed during 4 hours
  2. customthe reaction by TLC
  3. washwashed three times with water
  4. customThen the organic phase is evaporated under reduced pressure
  5. customThe crude thus obtained
  6. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-56180ba948ec454c8c53458f7d5bd6c4
Source dataset
uspto-grants-2013_03
Patent number
US08394797B2

Reaction notes

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