Ammonium Hydroxide → (-)-5,6,7,8-Tetrahydro-6-[(2-phenoxyethyl)propylamino]-1-naphthalenol

HRID 327586Notes

Reaction equation

HRID 327586 reaction equation
Cl.N1C=CC=CC=1.[CH2:8]([N:11]([CH:21]1[CH2:30][CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[O:31]C)[CH2:22]1)[CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:9][CH3:10].[NH4+].[OH-]>O>[CH2:8]([N:11]([CH:21]1[CH2:30][CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[OH:31])[CH2:22]1)[CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 10176127Pyridinium chlorideHCID 152288502-[N-n-propyl,N-2-(phenyloxy)ethylamino]-5-methoxytetralin

Product 1

HCID 15228851(-)-5,6,7,8-Tetrahydro-6-[(2-phenoxyethyl)propylamino]-1-naphthalenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of pyridine hydrochloride and the product of Example 1 was heated in an oil bath at 200° C. When the reaction was complete (TLC), it was cooled, diluted with H2O, made basic with NH4OH and extracted with ether. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to flash chromatography (Silica: 8:2 pet ether/EtOAc). The product was dissolved in ether and converted to a hydrochloride salt by the addition of dry ether-HCl. Anal. Calcd. for C21H27NO2 ·HCl: C, 69.69; H, 7.80; N, 3.87. Found: C, 69.54; H, 7.90; N, 3.87. NMR of the free base (300 MHz, CDCl3): δ 7.3-6.6(m, 8H), 4.0(t, 2H), 3.2-2.5(m, 9H), 2.1(m, 1H), 1.7-1.4(m, 3H), 0.9(t, 3H).

Workup

  1. temperaturewas cooled
  2. extractionextracted with ether
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe product was dissolved in ether
  7. additionconverted to a hydrochloride salt by the addition of dry ether-HCl

Sources & evidence

ORD record
ord-e42ff429abfe404eb1e1ed3bfae6a71d
Source dataset
uspto-grants-1993_12
Patent number
US05274003

Reaction notes

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