Hydrochloric Acid → 1-Aminomethyl-5-acetoxy-3-phenyl-3,4dihydronaphthalene hydrochloride

HRID 982094Notes

Reaction equation

HRID 982094 reaction equation
C(O)=O.[NH2:4][CH2:5][C:6]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1.NCC1C2[C:29](=[C:30]([OH:35])C=CC=2)CC(C2C=CC=CC=2)C=1.[ClH:42]>C(OC(=O)C)(=O)C>[ClH:42].[NH2:4][CH2:5][C:6]1[C:15]2[C:10](=[C:11]([O:16][C:30](=[O:35])[CH3:29])[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 200690411-Aminomethyl-5-hydroxy-3-phenyl-3,4-dihydronaphthaleneHCID 200690431-Aminomethyl-5-hydroxy-3-phenyl-3,4-dihydronaphthalene formic acid salt

Product 1

HCID 200690701-Aminomethyl-5-acetoxy-3-phenyl-3,4dihydronaphthalene hydrochloride

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of 1-aminomethyl-5-hydroxy-3-phenyl-3,4-dihydronaphthalene formic acid salt, the product of Example 2, in acetic anhydride saturated with anhydrous hydrogen chloride is stirred at ambient temperature for 48 h. A solid is collected by filtration and washed with diethyl ether. Crystallization of the crude material is achieved by dissolving the powder in hot ethanol, adding water, filtering the solution hot and allowing it to cool. Filtration and drying of the solid collected affords 1-aminomethyl-5-acetoxy-3-phenyl-3,4dihydronaphthalene hydrochloride.

Workup

  1. filtrationA solid is collected by filtration
  2. washwashed with diethyl ether
  3. customCrystallization of the crude material
  4. dissolutionby dissolving the powder in hot ethanol
  5. additionadding water
  6. filtrationfiltering the solution hot
  7. temperatureto cool
  8. filtrationFiltration
  9. customdrying of the solid
  10. customcollected

Sources & evidence

ORD record
ord-7146eb8919b24b5283fe3bd2333e53fd
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

Loading…