Methanol → HCID 22132544, compound

HRID 1856789Notes

Reaction equation

HRID 1856789 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]([CH2:14][CH2:15][CH2:16][CH2:17][NH:18]C(=O)C(F)(F)F)[CH2:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][N:10]([CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 22132521HCID 22132521, compound

Product 1

HCID 22132544HCID 22132544, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7-acetyl-2-(4-trifluoroacetamidobutyl)-1,2,3,4-tetrahydroisoquinoline (0.360 g, 1.05 mmol) was added to a stirred mixture of methanol (10 ml), water (1.5 ml) and potassium carbonate (0.769 g, 5.56 mmol) and heated at reflux for 1 h. The mixture was cooled then evaporated in vacuo and the residue partitioned between water (100 ml) and dichloromethane (50 ml). The aqueous phase was washed with dichloromethane (2×50 ml). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to afford the title compound as a yellow oil (0.178 g, 68%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. temperatureThe mixture was cooled
  4. customthen evaporated in vacuo
  5. customthe residue partitioned between water (100 ml) and dichloromethane (50 ml)
  6. washThe aqueous phase was washed with dichloromethane (2×50 ml)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-4e524168e64449f49cc677da3bf5fb8b
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

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