Hydrazine hydrate (1:1) → (3S)-1-[4-amino-3-(methyloxy)phenyl]-3-piperidinol

HRID 419540Notes

Reaction equation

HRID 419540 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH2:15][C@H:14]([OH:18])[CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.O.NN>CO>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([N:12]2[CH2:17][CH2:16][CH2:15][C@H:14]([OH:18])[CH2:13]2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59860244HCID 59860244, compound

Product 1

HCID 59860257(3S)-1-[4-amino-3-(methyloxy)phenyl]-3-piperidinolYield 74.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3S)-1-[3-(methyloxy)-4-nitrophenyl]-3-piperidinol (3.90 g, 15.5 mmol), FeCl3 (0.630 g, 3.9 mmol), activated carbon (4.0 g), and hydrazine hydrate (3.9 mL, 124 mmol) was heated in MeOH (100 mL) for 3 h. Once the starting material was judged consumed by TLC, the mixture was filtered over celite and concentrated to afford the title compound of step B as a dark purple solid (2.56 g, 11.53 mmol, 74% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.62-1.72 (m, 2H), 1.75 (d, J=3.30 Hz, 1H), 1.93 (td, J=8.07, 4.40 Hz, 1H), 2.44 (s, 2H), 2.88 (s, 1H), 2.93 (d, J=9.53 Hz, 1H), 2.99 (dd, J=10.81, 6.05 Hz, 2H), 3.12 (d, J=10.63 Hz, 1H), 3.84 (s, 3H), 3.95 (s, 1H), 6.44 (d, J=8.07 Hz, 1H), 6.53 (s, 1H), 6.64 (d, J=8.07 Hz, 1H).

Workup

  1. customOnce the starting material was judged consumed by TLC
  2. filtrationthe mixture was filtered over celite and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e00bf9859b7042ef9f8829dfec07a76a
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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