Hydrochloric Acid → HCID 14750911, compound

HRID 467313Notes

Reaction equation

HRID 467313 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].[CH2:14]([NH:21][CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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 refluxed for three hours. The mixture is evaporated to dryness, the oily residue is taken up with 100 ml of methanol and to the solution thus obtained 8.5 g of sodium borohydride are cautiously added at 0°-5° C. The mixture is left under stirring at room temperature for a night, then added with 50 ml of water and left under stirring for 30 minutes. The solvent is evapored, the residue is taken up with 30 ml of water and 10 ml of a concentrated solution of ammonium hydroxide. After extraction with 200 ml of ethyl acetate, the organic phase is dried over sodium sulfate, filtered and evaporated to dryness. A dark coloured oil is obtained, which is purified by flash chromatography using a mixture ethyl acetate/methanol 95/5 as an eluent. The base so obtained is converted into its hydrochloride by solution in 40 ml of isopropanol and addition of isopropanol saturated with hydrogen chloride to give 11.4 g of 2-benzylamino-7-methoxytetraline hydrochloride; m.p. 265°-267° C. (dec.).

Workup

  1. customThe mixture is evaporated to dryness
  2. additionare cautiously added at 0°-5° C
  3. waitThe mixture is left
  4. additionadded with 50 ml of water
  5. waitleft
  6. stirringunder stirring for 30 minutes
  7. extractionAfter extraction with 200 ml of ethyl acetate
  8. dry with materialthe organic phase is dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customA dark coloured oil is obtained
  12. customwhich is purified by flash chromatography
  13. customThe base so obtained

Sources & evidence

ORD record
ord-29f5f79fec9642c3b3e9caef810b25f8
Source dataset
uspto-grants-1992_10
Patent number
US05159103

Reaction notes

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