Morpholine → 1-Morpholinomethyl-3-phenylindazole

HRID 1730942Notes

Reaction equation

HRID 1730942 reaction equation
O[CH2:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4]1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.[OH-].[Na+]>C(O)C>[O:21]1[CH2:22][CH2:23][N:18]([CH2:2][N:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:4]2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 14798Sodium HydroxideHCID 132925841-Hydroxymethyl-3-phenylindazole

Product 1

HCID 214942361-Morpholinomethyl-3-phenylindazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Hydroxymethyl-3-phenylindazole (2 g), morpholine (0.84 g) and 5% aqueous sodium hydroxide solution (1 ml) were dissolved in ethanol (30 ml), and the mixture was heated under reflux for 3 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. The resulting oily residue was treated with ether-hydrochloric acid to obtain 1-morpholinomethyl-3-phenylindazole having a melting point between 166°-167° C (decomposition) after recrystallization from ethanol-ether.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customAfter completion of the reaction
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionThe resulting oily residue was treated with ether-hydrochloric acid

Sources & evidence

ORD record
ord-4d32cee2be6f4e29b39e499a7dd19fa3
Source dataset
uspto-grants-1976_11
Patent number
US03994890

Reaction notes

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