Hydrochloric Acid → HCID 14750911, compound

HRID 1614751Notes

Reaction equation

HRID 1614751 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)=[CH:5][CH:4]=1.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(C)C(S(O)(=O)=O)=CC=CC=1.[ClH:33]>C(O)(C)C.C1(C)C=CC=CC=1>[ClH:33].[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([NH:21][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 69252-Methylbenzenesulfonic acidHCID 7504BenzylamineHCID 777857-Methoxy-2-tetralone

Product 1

HCID 14750911HCID 14750911, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent2×

Procedure

A mixture of 8 g of 7-methoxy-2-tetralone, 4.8 g of benzylamine, 150 ml of anhydrous toluene and 100 mg of p.toluenesulfonic acid is heated with reflux. The residual oil is evaporated to dryness, taken up with 100 ml of methanol then 8.5 g of sodium borohydride are carefully added to the solution at 0°-5° C. The mixture is left under stirring at room temperature overnight, then 50 ml of water are added thereto. The solution is left under stirring for 30 minutes, the solvent is evaporated, the residue is taken up with 30 ml of water and 10 ml of a concentrated ammonium hydroxide solution. The product is extracted with 200 ml of ethyl acetate, the organic phase is dried over sodium sulfate, filtered and evaporated to dryness. A dark oil is obtained that is purified by flash chromatography (elution with a 95/5 mixture of ethyl acetate/methanol). The base thus obtained is transformed into its hydrochloride by dissolving it in 40 ml of isopropanol and by adding isopropanol saturated with hydrogen chloride. Thus, there is obtained 11.4 g of 7-methoxy-2-benzylamino-1,2,3,4-tetrahydronaphtalene hydrochloride; m.p. 265°-267° C. (dec.).

Workup

  1. temperaturewith reflux
  2. customThe residual oil is evaporated to dryness
  3. addition8.5 g of sodium borohydride are carefully added to the solution at 0°-5° C
  4. waitThe mixture is left
  5. addition50 ml of water are added
  6. waitThe solution is left
  7. stirringunder stirring for 30 minutes
  8. customthe solvent is evaporated
  9. extractionThe product is extracted with 200 ml of ethyl acetate
  10. dry with materialthe organic phase is dried over sodium sulfate
  11. filtrationfiltered
  12. customevaporated to dryness
  13. customA dark oil is obtained
  14. customthat is purified by flash chromatography (
  15. washelution
  16. additionwith a 95/5 mixture of ethyl acetate/methanol)
  17. customThe base thus obtained

Sources & evidence

ORD record
ord-a1d737771cff4ea4a7210b69ed5d809f
Source dataset
uspto-grants-1993_03
Patent number
US05198586

Reaction notes

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