Red-Al → 1-(4-Methoxyphenyl)piperidin-4-amine

HRID 634780Notes

Reaction equation

HRID 634780 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][C:12](=[N:15]O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([NH2:15])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 16684438Red-AlHCID 212604531-(4-Methoxy-phenyl)-piperidin-4-one oxime

Product 1

HCID 246902051-(4-Methoxyphenyl)piperidin-4-amineYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 1-(4-methoxy-phenyl)-piperidin-4-one oxime (4.55 g, 20.6 mmol), “Red-Al®” (70% in toluene, 23.4 ml) and toluene (10 ml) was heated at 140° for 2 h. After cooling, the reaction mixture was poured on H2O (100 ml). Extraction of the solution with CH2Cl2, drying of the organic layer, evaporation of the solvent and purification of the residue by chromatography (SiO2, CH2Cl2—MeOH—aq. NH3 140:10:1) gave 1-(4-methoxy-phenyl)-piperidin-4-yl-amine (3.5 g, 89%, white crystals, MS: m/e=207.2 (M+H+)).

Workup

  1. temperaturewas heated at 140° for 2 h
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured on H2O (100 ml)
  4. extractionExtraction of the solution with CH2Cl2
  5. dry with materialdrying of the organic layer, evaporation of the solvent and purification of the residue by chromatography (SiO2, CH2Cl2—MeOH—aq. NH3 140:10:1)

Sources & evidence

ORD record
ord-3f133142c2e84735aefa8961a3a3895c
Source dataset
uspto-grants-2001_02
Patent number
US06184236B2

Reaction notes

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