Morpholine → HCID 14839520, compound

HRID 2260022Notes

Reaction equation

HRID 2260022 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:17]=[CH:16][C:12]=2[C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:19]=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[CH:17]=[CH:16][C:12]=2[C:13]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 14839519HCID 14839519, compound2×

Product 1

HCID 14839520HCID 14839520, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

2-(3,4-Dimethoxyphenyl)-4-(4-fluorophenyl)-benzoic acid (compound 204 1.6 g; 0.00454 mole), tetrahydrofuran (50 ml) and diimidazolecarbonyl (0.92 g; 0.0057 mole) are introduced into a 100 ml flask. The mixture is stirred at 20° C. for 2 hours. Morpholine (1 ml; 0.0113 mole) is then added and the mixture is maintained under stirring for six hours. The reaction mixture is poured into distilled water (150 ml) and the precipitate is filtered, washed with water (100 ml) and then dried in the air. 2-(3,4-Dimethoxyphenyl)-4-(4-fluorophenyl)-1-morpholinocarbonylbenzene (1.3 g; yield: 68.4%) in thus obtained in the form of a white solid of m.p. 153° C. (compound 201).

Workup

  1. temperaturethe mixture is maintained
  2. stirringunder stirring for six hours
  3. additionThe reaction mixture is poured
  4. distillationinto distilled water (150 ml)
  5. filtrationthe precipitate is filtered
  6. washwashed with water (100 ml)
  7. customdried in the air

Sources & evidence

ORD record
ord-55661ef930dd4f2c90bed2faac618da5
Source dataset
uspto-grants-1995_12
Patent number
US05475132

Reaction notes

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