HCID 5029614, compound → 105315-95-5

HRID 523090Notes

Reaction equation

HRID 523090 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>CCO.CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 1

HCID 5029614HCID 5029614, compound

Product 1

HCID 18549575105315-95-5Yield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of 4-(3-chloro-4-nitrophenyl)morpholine (Preparation 112, 450 mg, 1.854 mmol) in EtOH/EtOAc (1:1, 30 mL) was passed through a 10% Pd/C cartridge using an H-cube (atmospheric H2, room temperature, 1 mL/min). The reaction mixture was concentrated in vacuo. The residue was purified by reverse phase column chromatography eluting with 0-20% MeCN in water to afford the title compound (150 mg, 38%).

Workup

  1. customan H-cube (atmospheric H2, room temperature, 1 mL/min)
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by reverse phase column chromatography
  4. washeluting with 0-20% MeCN in water

Sources & evidence

ORD record
ord-b795b2989fe849b3ad3ce90923507d06
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

Loading…