1-{[trans-4-(2,4-Dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}piperidin-4-ol → 1-{[trans-5-Amino-4-(2,4-dichlorophenyl)cyclohex-1-en-1-yl]methyl}piperidin-4-ol

HRID 1172338Notes

Reaction equation

HRID 1172338 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C@H:14]([N+:15]([O-])=O)[CH2:13][C:12]([CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]2)=[CH:11][CH2:10]1>[Zn].CO.C(O)(=O)C>[NH2:15][C@@H:14]1[CH2:13][C:12]([CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]2)=[CH:11][CH2:10][C@H:9]1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 1

HCID 687683961-{[trans-4-(2,4-Dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}piperidin-4-ol

Product 1

HCID 687699591-{[trans-5-Amino-4-(2,4-dichlorophenyl)cyclohex-1-en-1-yl]methyl}piperidin-4-olYield 76%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of Example 16A (50 mg, 0.13 mmol) in mixture of methanol/acetic acid (0.5 mL/0.5 mL), Zn powder (85 mg, 1.3 mmol) was added at room temperature. The reaction mixture was stirred for thirty minutes, filtered, concentrated under reduced pressure and purified by high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid) to provide the title compound (35 mg, 76%). 1H NMR (300 MHz, methanol-d4) δ ppm 7.54-7.61 (m, 1H), 7.39-7.49 (m, 2H), 6.14-6.34 (m, 1H), 3.89-4.02 (m, 1H), 3.73-3.84 (m, 1H), 3.51-3.69 (m, 1H), 2.36-3.13 (m, 3H), 1.91-2.19 (m, 1H). MS (ESI) m/z 356 (M+H)+.

Workup

  1. additionwas added at room temperature
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. custompurified by high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-0aeedafce894492da576f2a8413fe65b
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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