Methylamine → HCID 21519715, compound

HRID 1283295Notes

Reaction equation

HRID 1283295 reaction equation
[CH:1]12[C:13](=O)[CH:5]3[C:6]4[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=4[CH:8]1[CH:2]2[C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=13.[CH3:19][NH2:20].[BH4-].[Na+]>CO.C(O)C>[CH3:19][NH:20][CH:1]1[CH:8]2[C:2]3[C:3]([CH2:18][CH:17]=[CH:16][CH:15]=3)=[C:4]3[CH:13]1[CH:5]3[C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=12

Participants

6

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 12117541HCID 12117541, compound

Product 1

HCID 21519715HCID 21519715, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

An amount of 11.6 g (0.05 mole) of 1,1a,6,10b-tetrahydro-1,6-methano-dibenzo[a,e]cyclopropa[c]cyclohepten-11-one [V. Ioan, M. Popovici et al.: Tetrahedron Letters 38, 3383 (1965)] is dissolved in 200 ml of methanol, and 50 ml of a 33% solution of methylamine in ethanol added; the whole is heated, with stirring, to 35°, and subsequently stirred for a further hour at ca. 20°, whereby a thick precipitate is formed. There is then introduced into the reaction mixture with stirring, 3.8 g (0.1 mole) of sodium borohydride, with the temperature being maintained at 20° by cooling. The reaction mixture is subsequently stirred for one hour at 20° and then briefly refluxed. After cooling, the reaction mixture is completely concentrated in a waterjet vacuum. The residue is distributed between water and ether, and the ethereal phase extracted with 2N hydrochloric acid. The combined acidified extracts are rendered alkaline with concentrated ammonia and extracted with ether; the combined ether extracts are washed with water, dried over sodium sulphate and concentrated in a waterjet vacuum to obtain N-methyl-1,1a,6,10-tetrahydro-1,6-methano-dibenzo[a,e]cyclopropa[c]cycloheptene-11-amine; M.P. 142°-143°.

Workup

  1. temperaturethe whole is heated
  2. stirringsubsequently stirred for a further hour at ca. 20°
  3. customwhereby a thick precipitate is formed
  4. additionThere is then introduced into the reaction mixture
  5. stirringwith stirring
  6. temperatureby cooling
  7. stirringThe reaction mixture is subsequently stirred for one hour at 20°
  8. temperaturebriefly refluxed
  9. temperatureAfter cooling
  10. concentrationthe reaction mixture is completely concentrated in a waterjet vacuum
  11. extractionthe ethereal phase extracted with 2N hydrochloric acid
  12. extractionextracted with ether
  13. washthe combined ether extracts are washed with water
  14. dry with materialdried over sodium sulphate
  15. concentrationconcentrated in a waterjet vacuum

Sources & evidence

ORD record
ord-0f9c43302df343a7ab54930806100031
Source dataset
uspto-grants-1976_08
Patent number
US03974284

Reaction notes

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