Hydrochloric Acid → 5,6-Bis(acetoxy)-1-aminomethyl-3-phenyl-3,4-dihydronaphthalene hydrochloride
Reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]1[C:13]2[C:8](=[C:9]([OH:15])[C:10]([OH:14])=[CH:11][CH:12]=2)[CH2:7][CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:5]=1.Cl.C([O:25][CH2:26][CH3:27])C.[C:28](OC(=O)C)(=[O:30])[CH3:29]>>[ClH:1].[NH2:2][CH2:3][C:4]1[C:13]2[C:8](=[C:9]([O:15][C:26](=[O:25])[CH3:27])[C:10]([O:14][C:28](=[O:30])[CH3:29])=[CH:11][CH:12]=2)[CH2:7][CH:6]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:5]=1Participants
Procedure
A suspension of 7.6 g (25 mmol) of 1-aminomethyl-3,4-dihydro-5,6-dihydroxy-3-phenyl-naphthalene hydrochloride (Example 2B) in 400 mL of acetic anhydride saturated with anhydrous hydrogen chloride was stirred at ambient temperature for 48 h. Diethyl ether (approximately 2 L) was added and a solid was collected by filtration and washed with diethyl ether. Crystallization of the crude material (6.7 q) was achieved by dissolving the powder in 400 mL of hot ethanol, adding 100 mL of water, filtering the solution hot and allowing it to cool. The white crystals which formed were filtered and dried to give 2.8 g (29% yield) of 1-aminomethyl-5,6-bis(acetoxy)-3,4-dihydro-3-phenyl-naphthalene hydrochloride, m.p. 207°-208° C. 1H NMR (d6DMSO) delta 2.28 (s, 6H), 2.62 (dd, 1H), 2.95 (dd, 1H), 3.7-3.8 (m, 1H), 3.97 (s, 2H), 6.25 (d, 1H), 7.19 (d, 1H), 7.2-7.4 (m, 6H), 8.41 (br s, 3H).
Workup
- filtrationa solid was collected by filtration
- washwashed with diethyl ether
- customCrystallization of the crude material (6.7 q)
- dissolutionby dissolving the powder in 400 mL of hot ethanol
- additionadding 100 mL of water
- filtrationfiltering the solution hot
- temperatureto cool
- customThe white crystals which formed
- filtrationwere filtered
- customdried
Sources & evidence
- ORD record
- ord-058203e6ba7f4c8a8ace85c04d5e8ea6
- Source dataset
- uspto-grants-1990_10
- Patent number
- US04963568
Reaction notes
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