Allylamine → HCID 70568524, compound

HRID 1863514Notes

Reaction equation

HRID 1863514 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[NH:5][CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1S(O)(=O)=O.[CH2:21]([NH2:24])[CH:22]=[CH2:23]>O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[NH:5][C@@H:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[NH:24][CH2:21][CH:22]=[CH2:23]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 20556431HCID 20556431, compound

Product 1

HCID 70568524HCID 70568524, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.20 mole of 3,4-dichloro-N-(2-sulfocycloheptyl)aniline and 250 ml. of a 50 percent allylamine in water solution is heated at 125° C. in an autoclave for forty-eight hours. The resulting reaction mixture is washed from the autoclave 1500 ml. solution of methanol. This solution is evaporated until material therefrom oils out as a separate layer. The oil is extracted with 500 ml. of methylene chloride. The organic layer is washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated to an orange oil. The oil is chromatographed on 600 ml. of silica gel eluting with 2 liters of chloroform and 4 liters of ethyl acetate. The ethyl acetate fraction is separated and evaporated to an oil; the trans-3,4-dichloro-N-[2-(N-allylamino)cycloheptyl]aniline. This amine oil is converted to its hydrochloride salt with excess ether-hydrogen chloride mixture and recrystallized from a mixture of 450 ml. of methanol and about 2000 ml. of ethyl ether to obtain trans-3,4-dichloro-N-[2-(N-allylamino)cycloheptyl]aniline hydrochloride.

Workup

  1. customThe resulting reaction mixture
  2. washis washed from the autoclave 1500 ml
  3. customThis solution is evaporated until material
  4. extractionThe oil is extracted with 500 ml
  5. washThe organic layer is washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to an orange oil
  8. customThe oil is chromatographed on 600 ml
  9. customThe ethyl acetate fraction is separated
  10. customevaporated to an oil
  11. customrecrystallized from a mixture of 450 ml

Sources & evidence

ORD record
ord-c91e1347687c431fbfe614ad1e33b4dd
Source dataset
uspto-grants-1979_09
Patent number
US04169156

Reaction notes

Loading…