Ammonium formate → (5-Amino-2-(4-methylpiperazin-1-yl)phenyl)methanol

HRID 1190870Notes

Reaction equation

HRID 1190870 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=2[CH2:17][OH:18])[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[C:9]([CH2:17][OH:18])[CH:10]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 25918812[2-(4-Methylpiperazino)-5-nitrophenyl]methanol

Product 1

HCID 36995517(5-Amino-2-(4-methylpiperazin-1-yl)phenyl)methanolYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[2-(4-Methylpiperazin-1-yl)-5-nitrophenyl]methanol prepared in step A of example 1 (1.00 g, 3.98 mmol) was hydrogenated using ammonium formate (2.51 g, 10 eq) and Pd/C (10% Pd, 0.43 mg, 0.1 eq) in 50 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 an 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 (0.85 g, 97% yield).

Workup

  1. filtrationfiltered through a celite pad
  2. customThe filtrate was evaporated
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with an 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-9c2f6784ad24477b9389ca1675cf4541
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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