Toluene → HCID 86736363, compound

HRID 1391248Notes

Reaction equation

HRID 1391248 reaction equation
[O:1]=[C:2]1[C@@H:8]2[CH2:9][CH2:10][CH2:11][C@@:7]2([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH2:6][CH2:5][CH2:4][NH:3]1.[C:20]1(C)C=CC=CC=1.[NH2-].[Na+].CI>O>[O:1]=[C:2]1[C@H:8]2[CH2:9][CH2:10][CH2:11][C@@:7]2([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH3:20]

Participants

6

Reactant 4

HCID 1140Toluene3×HCID 6328Methyl iodideHCID 24533Sodium amideHCID 70607710HCID 70607710, compound

Product 1

HCID 86736363HCID 86736363, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 5.0 g. of dl-trans-1-oxo-5a-(3-methoxyphenyl)-decahydrocyclopent[c]azepine in 40 ml. of anhydrous toluene was added dropwise over thirty minutes to a stirred solution of 1.2 g. of sodium amide in 40 ml. of anhydrous toluene. The reaction mixture was heated at reflux for four hours, and then cooled to 25° C. and stirred while a solution of 4 g. of methyl iodide in 40 ml. of toluene was added in one portion. The reaction mixture was next heated to reflux and stirred for thirteen hours. After cooling the reaction mixture again to 25° C., 100 ml. of water was added dropwise over fifteen minutes. The aqueous layer was then separated, and the organic layer was washed with water, dried, and the solvent was removed by evaporation under reduced pressure to provide 5.3 g. of predominantly dl-cis-1-oxo-2-methyl-5a-(3-methoxyphenyl)-decahydrocyclopent[a]azepine. The product so formed was recrystallized three times from diisopropyl alcohol to afford pure dl-cis-1-oxo-2-methyl-5a-(3-methoxyphenyl)-decahydrocyclopent[ c]azepine. M.P. 103°-104° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for four hours
  3. temperatureThe reaction mixture was next heated
  4. temperatureto reflux
  5. stirringstirred for thirteen hours
  6. temperatureAfter cooling the reaction mixture again to 25° C.
  7. customThe aqueous layer was then separated
  8. washthe organic layer was washed with water
  9. customdried
  10. customthe solvent was removed by evaporation under reduced pressure
  11. customto provide 5.3 g
  12. customThe product so formed
  13. customwas recrystallized three times from diisopropyl alcohol

Sources & evidence

ORD record
ord-b961baff5eed4ce4b2c276942964d25f
Source dataset
uspto-grants-1979_02
Patent number
US04141893

Reaction notes

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