1,2,3,4-Tetrahydroisoquinoline → 4-(1,2,3,4-Tetrahydroisoquinolin-2-yl)-1-(1-naphthyloxy)-2-butanol Hydrochloride

HRID 64697Notes

Reaction equation

HRID 64697 reaction equation
[C:1]1([O:11][CH:12]([Cl:17])[CH:13]([OH:16])[CH2:14][CH3:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][NH:19]1>C(O)(C)C>[ClH:17].[CH2:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][N:19]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 212745841-(1-Naphthyloxy)-2-hydroxybutyl chloride

Product 1

HCID 131204504-(1,2,3,4-Tetrahydroisoquinolin-2-yl)-1-(1-naphthyloxy)-2-butanol Hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 12.5 g. (0.05 mole) of 1-(1-naphthyloxy)-2-hydroxybutyl chloride, 9.97 g. (0.075 mole) of 1,2,3,4-tetrahydroisoquinoline and 300 ml. of isopropanol was refluxed for 15 hr. On standing at room temperature a crystalline precipitate formed. The mixture was filtered and the filtrate concentrated to dryness under reduced pressure. The semi-solid residue which crystallized was recrystallized from acetone. The 12.2 g. of crystalline solid material melted at 169°-171° C.

Workup

  1. additionA mixture of 12.5 g
  2. customOn standing at room temperature
  3. customformed
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate concentrated to dryness under reduced pressure
  6. customThe semi-solid residue which crystallized
  7. customwas recrystallized from acetone

Sources & evidence

ORD record
ord-93002594eae4488f902f5436e4d21550
Source dataset
uspto-grants-1986_09
Patent number
US04609735

Reaction notes

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