Ammonium formate → HCID 59817772, compound

HRID 1190895Notes

Reaction equation

HRID 1190895 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH:10]=[C:11]([N+:13]([O-])=O)[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([O-])=O.[NH4+]>CCO.[Pd]>[N:1]1([C:7]2[CH:12]=[C:11]([CH:10]=[C:9]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[CH:8]=2)[NH2:13])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 11220089HCID 11220089, compound

Product 1

HCID 59817772HCID 59817772, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-[3-(morpholin-4-yl)-5-nitrophenyl]morpholine (123 mg, 0.42 mmol) was hydrogenated using ammonium formate (0.26 g, 10 eq) and Pd/C (10% Pd, 45 mg, 0.1 eq) in 4 mL of EtOH. The mixture was stirred overnight at room temperature and then filtered through a celite pad. The filtrate was evaporated and the residue was dissolved in DCM and washed with a saturated aqueous solution of Na2CO3. The aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated to yield expected compound as a brown powder (63 mg, 57% yield).

Workup

  1. filtrationfiltered through a celite pad
  2. customThe filtrate was evaporated
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with a saturated aqueous solution of Na2CO3
  5. extractionThe aqueous layer was extracted with DCM
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-9dd61415febb400a90c1ccff632441dc
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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