Triethylamine → HCID 13361800, compound

HRID 2413490Notes

Reaction equation

HRID 2413490 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.C(N(CC)CC)C.[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>C(Cl)Cl>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([Cl:19])=[CH:21][CH:22]=1)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 266981,2,3,4-Tetrahydroisoquinolin-6-ol

Product 1

HCID 13361800HCID 13361800, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.2 g of 6-hydroxy-1,2,3,4-tetrahydroisoquinoline are suspended in 50 ml of methylene chloride, 1.2 ml of triethylamine are added, and a solution of 1.4 g of 4-chlorobenzoyl chloride in 10 ml of methylene chloride is added dropwise with stirring and cooling. After standing overnight, the mixture is extracted by shaking with 2N hydrochloric acid and water, and the organic phase is dried and evaporated in a rotary evaporator. A colorless oil remains, and this crystallizes on trituration with ethyl acetate.

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted
  3. stirringby shaking with 2N hydrochloric acid and water
  4. customthe organic phase is dried
  5. customevaporated in a rotary evaporator
  6. customthis crystallizes on trituration with ethyl acetate

Sources & evidence

ORD record
ord-029ed2ada49f47b385f4e48456c283e1
Source dataset
uspto-grants-1988_01
Patent number
US04717724

Reaction notes

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