Hydrochloric Acid → HCID 20160887, compound

HRID 247464Notes

Reaction equation

HRID 247464 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=O)[CH2:7][CH2:6]2.[NH2:14][CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:17].[H][H].[ClH:26]>CO.C(O)(=O)C.C(O)(C)C.[Pt]>[ClH:26].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:14][CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:17])[CH2:7][CH2:6]2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 1000PhenylethanolamineHCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 20160887HCID 20160887, compoundYield 47.5%

Reagents, catalysts & solvents 4

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

An amount of 4 g of 6-methoxy-2-tetralone is reacted at 35° C. for 3 hours with 3.2 g of 2-amino-1-phenylethanol in 100 ml of methanol and 4 ml of glacial acetic acid in the presence of hydrogen and 0.3 g of platinum bioxide. After filtration and concentration, the residue is taken up with sodium hydroxide and extracted with ethyl acetate. The solution is dried over anhydrous sodium sulfate and evaporated. The black oil thus obtained is purified by flash-chromatography by utilizing a mixture of methylene chloride/methanol 9/1 as eluant. The fractions containing the product are collected and evaporated to dryness. The residue is dissolved in 20 ml of isopropyl alcohol and to the solution thus obtained there is added a saturated solution of hydrogen chloride in isopropyl alcohol. Thus, there is obtained the 2-[(6-methoxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-phenylethanol hydrochloride, designated by its code number SR 58280 A, which, after crystallization from isopropyl alcohol, melts at 174°-176° C. Yield: 47.5% of the theoretical value.

Workup

  1. filtrationAfter filtration and concentration
  2. extractionextracted with ethyl acetate
  3. dry with materialThe solution is dried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe black oil thus obtained
  6. customis purified by flash-chromatography
  7. additiona mixture of methylene chloride/methanol 9/1 as eluant
  8. additionThe fractions containing the product
  9. customare collected
  10. customevaporated to dryness
  11. dissolutionThe residue is dissolved in 20 ml of isopropyl alcohol and to the solution
  12. customthus obtained there

Sources & evidence

ORD record
ord-86a8cbfb8c8d4ce1a9bb3787ca08f21a
Source dataset
uspto-grants-1987_11
Patent number
US04707497

Reaction notes

Loading…