Ethanol → HCID 21184167, compound

HRID 1384991Notes

Reaction equation

HRID 1384991 reaction equation
[CH3:1][C:2]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=2)[CH:14]=[C:13]([CH3:26])[C:3]=1[O:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH3:12])[CH2:7]1.C(O)C.[H][H]>[Pt]=O.C(OCC)(=O)C>[NH2:23][C:19]1[CH:18]=[C:17]([C:15]2[CH:14]=[C:13]([CH3:26])[C:3]([O:4][CH2:5][CH:6]3[CH2:11][CH2:10][CH2:9][N:8]([CH3:12])[CH2:7]3)=[C:2]([CH3:1])[CH:16]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 18687480HCID 18687480, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21184167HCID 21184167, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[2,6-dimethyl-4-(3-nitrophenyl)phenoxymethyl]-1-methylpiperdine (785 mg, 2.21 mmol), ethanol (10 mL), and ethyl acetate (5 mL) was hydrogenated overnight with platinum oxide (50 mg) at 1 atmosphere of hydrogen. The reaction was purged with nitrogen and filtered through Celite. The solids were washed with methanol and ethyl acetate. The filtrate and the washings were concentrated to give 3-[4-(3-aminophenyl)-2,6-dimethylphenoxymethyl]-1-methylpiperidine as a yellow oil (735 mg, quantitative).

Workup

  1. customThe reaction was purged with nitrogen
  2. filtrationfiltered through Celite
  3. washThe solids were washed with methanol and ethyl acetate
  4. concentrationThe filtrate and the washings were concentrated

Sources & evidence

ORD record
ord-1f719d5f2ca143129ac7af9f79ccffef
Source dataset
uspto-grants-2001_07
Patent number
US06262078B1

Reaction notes

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