Trifluoroacetic acid → HCID 21463003, compound

HRID 1940571Notes

Reaction equation

HRID 1940571 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[CH:14]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[CH2:9][NH:8][CH2:17][CH2:16]3)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21473696HCID 21473696, compound

Product 1

HCID 21463003HCID 21463003, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(4-chlorophenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.5 g, 1.45 mmol) in dichloromethane (6 ml) was added trifluoroacetic acid (3 ml). The reaction mixture was stirred at room temperature for 1 h. The solvent was evaporated under reduced pressure and the residue partitioned between dichloromethane (3×20 ml) and 1N sodium hydroxide solution (30 ml). The combined organic phases were dried over potassium carbonate, filtered and evaporated under reduced pressure to give an oil. The oil was purified by flash chromatography using dichloromethane/methanol/ammonia 95:5:1 as eluant to afford the title compound as a solid (0.27 g, 76%); δH (CDCl3) 2.9 (2H, t, CH2), 3.24 (2H, t, CH2), 4.1 (2H, s, CH2), and 7.04-7.55 (7H, m, ArH).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between dichloromethane (3×20 ml) and 1N sodium hydroxide solution (30 ml)
  3. dry with materialThe combined organic phases were dried over potassium carbonate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give an oil
  7. customThe oil was purified by flash chromatography

Sources & evidence

ORD record
ord-b1623dbabfe54e4bbbc93c01edf12f2b
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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