Ethanol → 1-(4-Aminophenyl)-4-piperidinemethanol

HRID 1261889Notes

Reaction equation

HRID 1261889 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.C(O)C>[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][OH:17])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 23448266(1-(4-Nitrophenyl)piperidin-4-yl)methanol

Product 1

HCID 431331461-(4-Aminophenyl)-4-piperidinemethanol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a Round bottom flask, [A] [1-(4-Nitro-phenyl)-piperidin-4-yl]-methanol (5.021 g, 0.02125 mol), Ethanol (150 mL, 2.6 mol) and 10% Pd/C (10:90, Palladium:carbon black, 2.3 g, 0.0021 mol). The mixture was evacuated and charged with hydrogen via a balloon (3×). The reaction was stirred at RT under an atmosphere of Hydrogen over night. The solid was filtered and washed with Ethanol. The solvent was removed under vacuum to give [1-(4-Amino-phenyl)-piperidin-4-yl]-methanol a brown solid. The solid was triturated with Et2O to give a pink solid. NMR 1H (DSMO-d6)-6.68 (d, 2H, J=8.72 Hz), 6.47 (d, 2H J=8.68 Hz), 4.51 (bs, 2H), 4.43 (t, 1H, J=4.25 Hz), 3.22-3.40 (m, 4H), 2.43 (dt, 2H, JJ=2.24, 9.61 Hz) 1.70 (bd, 2H, J=11.15 Hz), 1.25-1.47 (m, 3H)

Workup

  1. customThe mixture was evacuated
  2. additioncharged with hydrogen via a balloon (3×)
  3. filtrationThe solid was filtered
  4. washwashed with Ethanol
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-9e3ac3e305b44f239b0dd52bde128a19
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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