HCID 12339189, compound → HCID 3045731, compound

HRID 1580144Notes

Reaction equation

HRID 1580144 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:24][CH:13]([N:14](CC4C=CC=CC=4)[CH:15]2[CH3:16])[CH2:12][CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[H][H]>[Pd].C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:24][CH:13]([NH:14][CH:15]2[CH3:16])[CH2:12][CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 12339189HCID 12339189, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 3045731HCID 3045731, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 7.21 g of 1-(3-methoxyphenyl)-6-benzyl-7-methyl-6-azabicyclo[3,2,1]octane, 2.2 g of colloid palladium and 165 ml of acetic acid is shaken at room temperature for 2 hours in a hydrogen atmosphere under atmospheric pressure. After the reaction is completed, the mixture is filtered to remove the catalyst. The filtrate is then evaporated to remove solvent. Water is added to the residue, and the aqueous mixture is made alkaline with ammonia. Then, the aqueous mixture is extracted with ether. The ether extract is dried and evaporated to remove solvent. 4.94 g of 1-(3-methoxyphenyl)-7-methyl-6-azabicyclo[3,2,1]octane are obtained. Hydrochloride: M.p. 174°-176°C(recrystallized from a mixture of acetone, ethanol and ether).

Workup

  1. filtrationthe mixture is filtered
  2. customto remove the catalyst
  3. customThe filtrate is then evaporated
  4. customto remove solvent
  5. additionWater is added to the residue
  6. extractionThen, the aqueous mixture is extracted with ether
  7. extractionThe ether extract
  8. customis dried
  9. customevaporated
  10. customto remove solvent

Sources & evidence

ORD record
ord-eaf8564e643d4fc298a3818350882c03
Source dataset
uspto-grants-1976_01
Patent number
US03932429

Reaction notes

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