4-Fluorobenzohydrazide → (S)-tert-Butyl 2-(4-((2-(4-fluorobenzoyl)hydrazono)methyl)phenyl)morpholine-4-carboxylate

HRID 710240Notes

Reaction equation

HRID 710240 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1)=O.[F:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([NH:29][NH2:30])=[O:28])=[CH:25][CH:24]=1>C(O)C>[F:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([NH:29][N:30]=[CH:1][C:3]2[CH:8]=[CH:7][C:6]([C@@H:9]3[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]3)=[CH:5][CH:4]=2)=[O:28])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 99724-FluorobenzohydrazideHCID 86654636(S)-tert-Butyl 2-(4-formylphenyl)morpholine-4-carboxylate

Product 1

HCID 89689421(S)-tert-Butyl 2-(4-((2-(4-fluorobenzoyl)hydrazono)methyl)phenyl)morpholine-4-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-tert-Butyl 2-(4-formylphenyl)morpholine-4-carboxylate (120 mg, 0.41 mmol) and 4-fluorobenzohydrazide (64 mg, 0.41 mmol) were dissolved in ethanol (2 ml) and stirred for 2 h at room temperature. The solvent was evaporated and ether/ethanol (3:1) was added to precipitate the product. The crystals were filtered off to yield a white solid (101 mg, 58%). MS (ISP): 327.1 ([M-tBu+H]+).

Workup

  1. customThe solvent was evaporated
  2. additionether/ethanol (3:1) was added
  3. customto precipitate the product
  4. filtrationThe crystals were filtered off

Sources & evidence

ORD record
ord-c077579180d84225b5c0661010abf257
Source dataset
uspto-grants-2015_11
Patent number
US09181230B2

Reaction notes

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