Methylamine → HCID 12286607, compound

HRID 1580135Notes

Reaction equation

HRID 1580135 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:16]([O:18]C)=O)[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[CH3:20][NH2:21].[H][H]>C1C=CC=CC=1.[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:10][CH:11]([N:21]([CH3:20])[C:16]2=[O:18])[CH2:12][CH2:13][CH2:14]3)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 12339132HCID 12339132, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12286607HCID 12286607, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 241BenzeneSolvent

Procedure

A mixture of 9.29 g of methyl 1-(3-methoxyphenyl)-3-oxo-cyclohexane-1-carboxylate, 5.5 ml of 40 % aqueous methylamine and 0.13 g of platinum oxide is shaken at room temperature for 5 hours in a hydrogen atmosphere under atmospheric pressure. The mixture absorbs about 790 ml of hydrogen. After the reaction, the mixture is filtered to remove the catalyst. The filtrate is concentrated under reduced pressure. The residue thus obtained is heated at 100° to 110°C for 2 hours under reduced pressure, and then dissolved in benzene. The benzene solution is washed with 10 % hydrochloric acid and water, successively. Then, the benzene solution is evaporated to remove solvent. The residue thus obtained is recrystallized from isopropylether. 5.8 g of 1-(3-methoxyphenyl)-6-methyl-6azabicyclo[3,2,1]octane-7-one are obtained. M.p. 68° - 70°C.

Workup

  1. customThe mixture absorbs about 790 ml of hydrogen
  2. customAfter the reaction
  3. filtrationthe mixture is filtered
  4. customto remove the catalyst
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customThe residue thus obtained
  7. temperatureis heated at 100° to 110°C for 2 hours under reduced pressure
  8. washThe benzene solution is washed with 10 % hydrochloric acid and water
  9. customThen, the benzene solution is evaporated
  10. customto remove solvent
  11. customThe residue thus obtained
  12. customis recrystallized from isopropylether

Sources & evidence

ORD record
ord-f0b415af0e1a4d8ab8a75c461ba9c8e7
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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