1-(3-Methoxy-4-nitro-benzyl)-piperidin-4-ol → 1-[(4-Amino-3-methoxyphenyl)methyl]piperidin-4-ol

HRID 1262312Notes

Reaction equation

HRID 1262312 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1>[Pd].C(O)C>[NH2:17][C:16]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 667116861-(3-Methoxy-4-nitro-benzyl)-piperidin-4-ol

Product 1

HCID 574161131-[(4-Amino-3-methoxyphenyl)methyl]piperidin-4-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a par bottle, 1-(3-Methoxy-4-nitro-benzyl)-piperidin-4-ol (0.74 g, 2.8 mmol), Ethanol (20 mL) and 10% Pd/C (10:90, Palladium:carbon black, 0.30 g, 0.28 mmol) were added. The reaction mixture was evacuated and charged with hydrogen at 35 psi. The mixture was shaken for 3 hours. The solid was filtered through Celite and washed with methanol. The solvent was removed under vacuum to give 1-(4-Amino-3-methoxy-benzyl)-piperidin-4-ol as a semi-solid.

Workup

  1. customThe reaction mixture was evacuated
  2. additioncharged with hydrogen at 35 psi
  3. filtrationThe solid was filtered through Celite
  4. washwashed with methanol
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-042736b39a7540b09872451e76173697
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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