Hydrochloric Acid → HCID 12843084, compound

HRID 1732993Notes

Reaction equation

HRID 1732993 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.[CH:14]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[H][H].[ClH:23]>CC(C)=O.[Pt]=O.C(O)C>[ClH:23].[CH:14]1([NH:20][CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7965CyclohexylamineHCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 12843084HCID 12843084, compound

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 180AcetoneSolventHCID 702EthanolSolvent2×

Procedure

A mixture of 5.3 g of 6-methoxy-2-tetralone, 3 g of cyclohexylamine and 70 ml of absolute ethanol was heated for 7 hours at reflux. To the mixture was added 0.3 g of platinum oxide, and a catalytic reduction was conducted in the presence of hydrogen. After absorption of hydrogen gas was completed, the platinum oxide catalyst in the reaction solution was removed by filtration and the filtrate was concentrated under reduced pressure to obtain a residue. Then, an ethanol solution saturated with hydrogen chloride was added to the residue and the solution was concentrated under reduced pressure. The residue obtained was dissolved in acetone and the solution was stirred to form crystals. After collecting the crystals by filtration and recrystallizing from a mixed solvent of ethanol and diethyl ether, 5.0 g of N-cyclohexyl-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine hydrochloride was obtained as colorless needles having a melting point of 252°-254° C.

Workup

  1. temperaturewas heated for 7 hours
  2. temperatureat reflux
  3. customAfter absorption of hydrogen gas
  4. customthe platinum oxide catalyst in the reaction solution was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto obtain a residue
  7. concentrationthe solution was concentrated under reduced pressure
  8. customThe residue obtained
  9. customto form crystals
  10. customAfter collecting the crystals
  11. filtrationby filtration
  12. customrecrystallizing from a mixed solvent of ethanol and diethyl ether

Sources & evidence

ORD record
ord-9b49cc076cae45da8e5013f41bba56c5
Source dataset
uspto-grants-1980_12
Patent number
US04239903

Reaction notes

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