Benzenamine, 4-(4-morpholinyl)- → HCID 178517090, compound

HRID 352298Notes

Reaction equation

HRID 352298 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.O[CH:15]=[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:25]>O1CCCC1>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:13]=[CH:12][C:10]([NH:11][CH:15]=[C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][C:17]3=[O:25])=[CH:9][CH:8]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 1784187413-(hydroxymethylidene)-1H-indol-2-one

Product 1

HCID 178517090HCID 178517090, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4-morpholinoaniline (8.3 g, 51.5 mmol) in 100 mL of tetrahydrofuran was treated with 3-hydroxymethylene-1,3-dihydro-indol-2-one (5.5 g, 30.9 mmol) in one portion. The reaction mixture was heated at reflux for 3 h. The reaction mixture was concentrated. The residue was treated with 125 mL of ethyl acetate and the resulting suspension was heated at 40° C. for 2 h. The suspension was cooled to room temperature and the solid collected by suction filtration and washed with ethyl acetate. The solid obtained was dried under vacuum to give the title compound (10.1 g, 92%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationThe reaction mixture was concentrated
  4. additionThe residue was treated with 125 mL of ethyl acetate
  5. temperatureThe suspension was cooled to room temperature
  6. filtrationthe solid collected by suction filtration
  7. washwashed with ethyl acetate
  8. customThe solid obtained
  9. customwas dried under vacuum

Sources & evidence

ORD record
ord-0c47fed580b542b2ae71732cc363236b
Source dataset
uspto-grants-2004_06
Patent number
US06747025B1

Reaction notes

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