1,2,3,4-Tetrahydroisoquinoline → 1-(2-Chlorophenoxy)-4-(1,2,3,4-tetrahydroisoquinolyl)-2-butanol Hydrochloride Hydrate

HRID 1382393

Reaction equation

HRID 1382393 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH:5](Cl)[CH:6]([OH:9])[CH2:7][CH3:8].[CH2:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][NH:16]1.O.Cl>C(O)CCC>[OH2:4].[ClH:1].[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH2:5][CH:6]([OH:9])[CH2:7][CH2:8][CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][NH:16]1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 198402391-(o-Chlorophenoxy)-2-hydroxybutyl chlorideHCID 21885828Hydrate;hydrochloride

Product 1

HCID 212745811-(2-Chlorophenoxy)-4-(1,2,3,4-tetrahydroisoquinolyl)-2-butanol Hydrochloride Hydrate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 11.8 g. (0.05 mole) of 1-(2-chlorophenoxy)-2-hydroxybutyl chloride, 13.3 g. (0.1 mole) of 1,2,3,4-tetrahydroisoquinoline and 100 ml. of n-butanol was heated in a steel bomb at 120° C. for 24 hr. The reaction mixture was filtered at room temperature, the filtrate was mixed with 200 ml. 3N hydrochloric acid and extracted twice with 100 ml. isopropyl ether. The aqueous acidic solution was made basic and extracted with isopropyl ether and treated with ethereal hydrogen chloride. Recrystallization with isopropanol yielded 6 g. of the hydrochloride hydrate of the product which melted at 118°-120° C.

Workup

  1. additionA mixture of 11.8 g
  2. filtrationThe reaction mixture was filtered at room temperature
  3. additionthe filtrate was mixed with 200 ml
  4. extraction3N hydrochloric acid and extracted twice with 100 ml
  5. extractionextracted with isopropyl ether
  6. additiontreated with ethereal hydrogen chloride
  7. customRecrystallization with isopropanol
  8. customyielded 6 g

Sources & evidence

ORD record
ord-9bfb7643045647b98f7ad1e1d668f317
Source dataset
uspto-grants-1989_02
Patent number
US04806555

Linked notes

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