Ammonium formate → HCID 67247561, compound

HRID 1190880Notes

Reaction equation

HRID 1190880 reaction equation
[CH3:1][C:2]1[C:3]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)=[C:4]([CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.N1CCNCC1.C([O-])=O.[NH4+]>CCO.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:3]=1[N:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1)[NH2:8]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67247909HCID 67247909, compound

Product 1

HCID 67247561HCID 67247561, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-{[3-Methyl-2-(4-methylpiperazin-1-yl)-5-nitrophenyl]methyl}morpholine-piperazine (113 mg, 0.34 mmol) was hydrogenated using ammonium formate (213 mg, 10 eq) and Pd/C (10% Pd, 36 mg, 0.05 eq) in 5 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 pale yellow oil (92 mg, 89% 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-bc6c4fc41b1443b7b0167821fa968eac
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

Loading…