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

HRID 982092Notes

Reaction equation

HRID 982092 reaction equation
[NH2:1][CH2:2][C:3]1(O)[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:4]1.[ClH:22]>C(O)(C)C>[ClH:22].[NH2:1][CH2:2][C:3]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 200690361-Aminomethyl-1-hydroxy-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 200690961-Aminomethyl-5-methoxy-3-phenyl-3,4-dihydronaphthalene hydrochlorideYield 33%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-Aminomethyl-1-hydroxy-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene (2.0 g, 7.2 mmol), from Step 1, was heated at reflux temperature for 2 h in 75 mL of isopropyl alcohol saturated with hydrogen chloride. The resultant solution was concentrated and the solid residue was triturated with hot toluene to give 0.72 g (33% yield) of 1-aminomethyl-5-methoxy-3-phenyl-3,4-dihydronaphthalene hydrochloride, m.p. 193°-196° C.; 1H NMR (d6-DMSO) δ 2.78 (dd, 1H), 3.14 (dd, 1H), 3.2-3.5 (m, 2H+H2O), 3.84 (s, 3H), 3.93 (d, 1H), 6.2 (m, 1H), 6.54 (d, 1H), 6.60 (d, 1H), 6.75 (d, 1H), 7.2-7.5 (m, 5H).

Workup

  1. concentrationThe resultant solution was concentrated
  2. customthe solid residue was triturated with hot toluene

Sources & evidence

ORD record
ord-575a0725a5584697802b33c68a101bfa
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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