Ammonium formate → HCID 53328351, compound

HRID 1190878Notes

Reaction equation

HRID 1190878 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:12][C:11]([N+:20]([O-])=O)=[CH:10][C:9]=2[CH3:23])[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>CCO.[Pd]>[CH3:23][C:9]1[CH:10]=[C:11]([CH:12]=[C:13]([CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]=1[N:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1)[NH2:20]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 53328349HCID 53328349, compound

Product 1

HCID 53328351HCID 53328351, compoundYield 104%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Methyl-4-[2-methyl-4-nitro-6-(pyrrolidin-1-ylmethyl)phenyl]piperazine (90 mg, 0.28 mmol) was hydrogenated using ammonium formate (107 mg, 6 eq) and Pd/C (10% Pd, 15 mg, 0.05 eq) in 2 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 (84 mg, quantitative 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-e5d2e50b249740f59524d104f9c31bee
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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