Hydrochloric Acid → HCID 68423460, compound

HRID 453902Notes

Reaction equation

HRID 453902 reaction equation
FC(F)(F)C([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:11]=2)[CH2:6]1)=O.C(=O)([O-])[O-].[K+].[K+].[ClH:30].C(OCC)C>CO>[ClH:30].[ClH:30].[N:16]1([CH2:15][C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[CH2:6][NH:5][CH2:14][CH2:13]3)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 86761960HCID 86761960, compound

Product 1

HCID 68423460HCID 68423460, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,2,2-Trifluoro-1-(6-(piperidin-1-ylmethyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (1.88 g, 5.76 mmol) was dissolved in methanol (23 ml); potassium carbonate (1.99 g, 14.4 mmol) was added and the reaction mixture was stirred for 15 h at RT. The solvent was then removed under vacuum, and the residue was taken up in dichloromethane and washed with water (15 ml). The aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over sodium sulfate and concentrated under vacuum. The residue was taken up in an acetone/diethyl ether mixture, and the hydrochloride was precipitated with 2 M hydrogen chloride in diethyl ether (3 equiv.) and, after being filtered out with suction, was dried under vacuum. Yield: 1.62 g (93%)

Workup

  1. customThe solvent was then removed under vacuum
  2. washwashed with water (15 ml)
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. filtrationafter being filtered out with suction
  7. customwas dried under vacuum

Sources & evidence

ORD record
ord-c05b4b86853340aeb4c92f63559d1ae8
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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