Trifluoroacetic acid → HCID 66746279, compound

HRID 1019873Notes

Reaction equation

HRID 1019873 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([N:21]([CH2:23][C:24]2[CH:33]=[CH:32][C:27]3[O:28][CH2:29][CH2:30][O:31][C:26]=3[CH:25]=2)[CH3:22])[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[O:28]1[C:27]2[CH:32]=[CH:33][C:24]([CH2:23][N:21]([CH3:22])[CH:18]3[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]3)=[CH:25][C:26]=2[O:31][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66747178HCID 66747178, compound

Product 1

HCID 66746279HCID 66746279, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (591 μL, 7.67 mmol, 15.0 eq) is added at 0° C. to a stirred solution of 4-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-methyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (195 mg, 0.51 mmol, 1.0 eq) in dichloromethane (10 mL). After 3 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×10 mL) and water (10 mL) and the pH is adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford (2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-methyl-piperidin-4-yl-amine as a light yellow solid (148 mg, 99% yield).

Workup

  1. extractionthe reaction mixture is extracted with dichloromethane (3×10 mL) and water (10 mL)
  2. additionthe pH is adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a65cecebccad4cf881a56be6ae0f0075
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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