Ammonium formate → HCID 67247750, compound

HRID 1190894Notes

Reaction equation

HRID 1190894 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[C:10]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[CH:9]=2)[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>CCO.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[C:12]([CH:11]=[C:10]([N:17]3[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]3)[CH:9]=2)[NH2:14])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67248827HCID 67248827, compound

Product 1

HCID 67247750HCID 67247750, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-methyl-4-[3-(4-methylpiperazin-1-yl)-5-nitrophenyl]piperazine (258 mg, 0.81 mmol) was hydrogenated using ammonium formate (0.51 g, 10 eq) and Pd/C (10% Pd, 85 mg, 0.1 eq) in 8 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 (212 mg, 90% yield). m/z (MALDI-TOF) 290.2 [M+H]+.

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-25eef8a33f7e4a8cabe565af0994d3fc
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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