Trifluoroacetic acid → HCID 69553293, compound

HRID 2172218Notes

Reaction equation

HRID 2172218 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:25][C:23]([F:24])([F:26])[C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70873613HCID 70873613, compound

Product 1

HCID 69553293HCID 69553293, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[3-(4-Trifluoromethylphenyl)propyl]piperidine-1-carboxylic acid tert-butyl ester (13.45 g, 36.2 mmol) prepared in Reference Example 360 was dissolved in dichloromethane (50 ml). Trifluoroacetic acid (25 ml, 324 mmol) was added thereto and stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and adjusted to a pH of 10 using a 5 N sodium hydroxide aqueous solution. The mixture was subjected to extraction with dichloromethane 4 times. The result was dried over anhydrous sodium sulfate and then concentrated to afford the title compound as a pale brown oil (10.2 g, quant).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionThe mixture was subjected to extraction with dichloromethane 4 times
  3. dry with materialThe result was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ff43a6ec634a4c09b7ffa630c24793cc
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

Loading…