Hydrochloric Acid → HCID 19888695, compound

HRID 247465Notes

Reaction equation

HRID 247465 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[OH:4].[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][C:20](=O)[CH2:21]2)=[CH:16][CH:15]=1.C([BH3-])#N.[Na+].Cl>CO.C(O)(=O)C.C(O)(C)C.C(OCC)C>[ClH:11].[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][CH:20]([NH:1][CH2:2][CH:3]([C:5]3[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=3)[OH:4])[CH2:21]2)=[CH:16][CH:15]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 777857-Methoxy-2-tetraloneHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19888695HCID 19888695, compoundYield 40%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent2×

Procedure

A mixture of 4.8 g of 2-amino-1-(3-chlorophenyl)ethanol and 5 g of 7-methoxy-2-tetralone in 80 ml of methanol and 5 ml of glacial acetic acid is stirred at room temperature for three hours. Then 2.7 g of sodium cyanoborohydride are added thereto and the solution thus obtained is left under stirring for a night. The mixture is made acid and evaporated to dryness, then the residue is taken up with 40 ml of water made alkaline and extracted with 200 ml of ethyl acetate. The organic phase thus obtained is dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The oil thus obtained is purified by flash-chromatography using a mixture ethyl acetate/methanol 95/5 for the elution. To the solution thus obtained there is added 40 ml of isopropyl alcohol and 150 ml of ethyl ether, then some drops of isopropyl alcohol saturated with hydrogen chloride. Thus, there is obtained the 2-[(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-(3-chloropheny)ethanol hydrochloride, designated by its code number SR 58338 A, which, after crystillization from isopropyl alcohol, melts at 186°-188° C. Yield: 40% of the theoretical value.

Workup

  1. customthe solution thus obtained
  2. waitis left
  3. stirringunder stirring for a night
  4. customevaporated to dryness
  5. extractionextracted with 200 ml of ethyl acetate
  6. customThe organic phase thus obtained
  7. dry with materialis dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe oil thus obtained
  11. customis purified by flash-chromatography
  12. washfor the elution
  13. customTo the solution thus obtained there

Sources & evidence

ORD record
ord-90bdc93039464d71b8cb58c50a53cb1b
Source dataset
uspto-grants-1987_11
Patent number
US04707497

Reaction notes

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