Triethylamine → HCID 13361842, compound

HRID 2413502Notes

Reaction equation

HRID 2413502 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][NH:7][CH2:6][CH2:5]2.[CH3:12][O:13][C:14]1[CH:24]=[CH:23][C:17]([CH2:18][CH2:19][C:20](Cl)=O)=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:20][CH2:19][CH2:18][C:17]1[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:24][CH:23]=1)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 266981,2,3,4-Tetrahydroisoquinolin-6-olHCID 109324413-(4-Methoxyphenyl)propionyl chloride

Product 1

HCID 13361842HCID 13361842, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.4 g of 6-hydroxy-1,2,3,4-tetrahydroisoquinoline are acylated twice with 14.2 g of 4-methoxydihydrocinnamoyl chloride in methylene chloride in the presence of 7.5 g of triethylamine, the mixture is extracted by shaking with water, and the organic phase is dried and evaporated in a rotary evaporator. The crude product is dissolved, without further purification, in tetrahydrofuran, and added dropwise, with cooling, to a solution of 1.5 g of lithium aluminum hydride in dry tetrahydrofuran. After destroying the reagent with water, inorganic material is filtered off and the filtrate is dried. The residue from filtration is dried, extracted twice by boiling with methanol, and the methanol and tetrahydrofuran are evaporated together in a rotary evaporator. After triturating the oily residue with ethyl acetate, 3.5 g of colorless product (33% of theory) are obtained. Melting point: 163°-164°.

Workup

  1. extractionthe mixture is extracted
  2. customthe organic phase is dried
  3. customevaporated in a rotary evaporator
  4. dissolutionThe crude product is dissolved, without further purification, in tetrahydrofuran
  5. additionadded dropwise
  6. temperaturewith cooling, to a solution of 1.5 g of lithium aluminum hydride in dry tetrahydrofuran
  7. customAfter destroying the reagent with water, inorganic material
  8. filtrationis filtered off
  9. customthe filtrate is dried
  10. filtrationThe residue from filtration
  11. customis dried
  12. extractionextracted twice
  13. customthe methanol and tetrahydrofuran are evaporated together in a rotary evaporator
  14. customAfter triturating the oily residue with ethyl acetate, 3.5 g of colorless product (33% of theory)
  15. customare obtained

Sources & evidence

ORD record
ord-5d7321199cdf4e0b84a46a09581e0a27
Source dataset
uspto-grants-1988_01
Patent number
US04717724

Reaction notes

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