Methylamine → HCID 12339148, compound

HRID 1580134Notes

Reaction equation

HRID 1580134 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:16]([O:18][CH3:19])=[O:17])[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]>[Pt]=O.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:13][CH2:12][CH:11]([NH:21][CH3:20])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

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

Product 1

HCID 12339148HCID 12339148, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.52 g of methyl 1-(3-methoxyphenyl)-3-oxo-cyclohexane-1-carboxylate, 0.5 ml of 30% aqueous methylamine, 8 ml of methanol and 0.025 g of platinum oxide is shaken for 48 hours in a hydrogen atmosphere. After the reaction, the mixture is filtered to remove the catalyst. The filtrate is concentrated under reduced pressure to remove solvent, whereby methyl 1-(3-methoxyphenyl)-3-methylamino-cyclohexane-1-carboxylate is obtained as crude oil. 7 ml of xylene are added to the crude oil and the mixture is refluxed for 20 hours under heating. Then, the mixture is concentrated under reduced pressure to remove solvent. The residue is dissolved in ether. The ether solution is washed with 10 % hydrochloric acid and water, successively, dried and then evaporated to remove solvent. The residue thus obtained is recrystallized from n-hexane. 0.33 g of 1-(14 3-methoxyphenyl)-6-methyl-6-azabicyclo[3,2,1]octane-7-one is obtained. M.p. 68° - 70°C.

Workup

  1. customAfter the reaction
  2. filtrationthe mixture is filtered
  3. customto remove the catalyst
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customto remove solvent

Sources & evidence

ORD record
ord-6b8094b7e72240bfa5512aba450fa827
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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