Hydrochloric Acid → HCID 19961156, compound

HRID 233387Notes

Reaction equation

HRID 233387 reaction equation
[NH2:1][CH2:2][C:3]1(O)[C:12]2[C:7](=[C:8]([O:15][CH3:16])[C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH2:6][CH:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:4]1.[ClH:24]>C(O)(C)C>[ClH:24].[NH2:1][CH2:2][C:3]1[C:12]2[C:7](=[C:8]([O:15][CH3:16])[C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH2:6][CH:5]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19961233HCID 19961233, compound

Product 1

HCID 19961156HCID 19961156, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-Aminomethyl-5,6-dimethoxy-1-hydroxy-3-phenyl-1,2,3,4-tetrahydronaphthalene (11.5 g, 37 mmol), from Step 1, was heated at reflux temperature in 300 mL of isopropyl alcohol saturated with hydrochloric acid for 2 h. The resultant solution was concentrated and the solid residue was triturated with hot toluene to give 10.6 g (98% yield) of 1-aminomethyl-5,6-dimethoxy-3-phenyl-3,4-dihydronaphthalene hydrochloride, m.p. 189.5°-190° C.; 1H NMR (d6 -DMSO) δ: 2.78 (dd, 1H), 3.11 (dd, 1H), 3.2-3.4 (m, 2H+H2O), 3.6 (s, 3H), 3.81 (s, 3H), 3.93 (d, 1H), 6.1 (d, 1H), 6.93 (d, 1H), 7.12 (d, 1H), 7.2-7.4 (m, 5H).

Workup

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

Sources & evidence

ORD record
ord-d5fe31f09bff4a4cbf1a7d67c8aa90c4
Source dataset
uspto-grants-1997_01
Patent number
US05591884

Reaction notes

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