Trifluoroacetic acid → HCID 68771739, compound

HRID 1174528Notes

Reaction equation

HRID 1174528 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]([C:17](=[O:27])[N:18]([CH3:26])[CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:26][N:18]([CH:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)[C:17]([CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8][CH2:9]1)=[O:27]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 687717603-[Methyl-(1-methyl-piperidin-4-yl)-carbamoyl]-2,3-dihydro-indole-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 68771739HCID 68771739, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-[Methyl-(1-methyl-piperidin-4-yl)-carbamoyl]-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (C) (3.93 g, 10.53 mmol) in dichloromethane (20 cm3) was cooled to 0° C. in an ice/water bath and trifluoroacetic acid (10 cm3) added. The solution was stirred at 0° C. for 1 hr before warming to room temperature. The solution was made basic with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane (3×100 cm3). The organic layer was then dried over magnesium sulfate, filtered and evaporated under reduced pressure to afford the title compound (D) (2.79 g, 10.2 mmol, 97%).

Workup

  1. temperaturebefore warming to room temperature
  2. extractionextracted with dichloromethane (3×100 cm3)
  3. dry with materialThe organic layer was then dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-dbe1cc4f0cbb451c812686a2852b5f0d
Source dataset
uspto-grants-2010_11
Patent number
US07838518B2

Reaction notes

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