N-Aminomorpholine → HCID 87378600, compound

HRID 2409454Notes

Reaction equation

HRID 2409454 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:15]3[NH:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:17])[N:8]([CH2:18][O:19][CH3:20])[C:7]=2[CH:6]=[C:5]([CH:21]=O)[CH:4]=1.[NH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:16]2[C:15]3[NH:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:17])[N:8]([CH2:18][O:19][CH3:20])[C:7]=2[CH:6]=[C:5](/[CH:21]=[N:23]/[N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:4]=1

Participants

4

Reactant 2

HCID 20315N-AminomorpholineHCID 86657391HCID 86657391, compound

Product 1

HCID 87378600HCID 87378600, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound (95 mg, 0.31 mmol) prepared in step 1 was dissolved in toluene (10 ml), added with 4-aminomorpholine (0.031 ml, 0.31 mmol) at room temperature. The resulting mixture was then heated and allowed to reflux under dean-stark condenser for 5 hours. After cooling to room temperature, the solivent was removed under reduced pressure and the residue was purified by flash column chromatography (dichloromethane:methanol=20:1) to obtain the title compound (109 mg, yield: 89%, yellow solid).

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureto reflux under dean-stark condenser for 5 hours
  3. customthe solivent was removed under reduced pressure
  4. customthe residue was purified by flash column chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-425e23a33ea44edaa69410109f9f935a
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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