Trifluoroacetic acid → HCID 86585549, compound

HRID 720901Notes

Reaction equation

HRID 720901 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:35])[NH:15][CH:16]([CH2:26][CH2:27][CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[CH2:17][CH2:18][CH2:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][CH2:18][CH2:17][CH:16]([NH:15][C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:35])[CH2:26][CH2:27][CH2:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68838775HCID 68838775, compound

Product 1

HCID 86585549HCID 86585549, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[4-(3-Pyridyl)-1-(3-pyridyl-propyl)-butylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (59) (0.3754 g; 0.78 mmol) is dissolved in methylene chloride (6 mL) at ambient temperature. Trifluoroacetic acid (6 mL) is added in a slow stream, and the solution is stirred for 90 minutes at ambient temperature. The solution is concentrated in vacuo at 40° C. The residue is slurried in a mixture of methylene chloride (10 mL) and water (50 mL), then potassium carbonate is added until the slurry is alkaline. The slurry is diluted with water (50 mL) then extracted with methylene chloride (3×10 mL). The organic extracts are dried over MgSO4, filtered, and concentrated in vacuo affording the desired product (0.1704 g) as a yellow oil. ESMS:MH+ 382.4 (base).

Workup

  1. concentrationThe solution is concentrated in vacuo at 40° C
  2. additionThe residue is slurried in a mixture of methylene chloride (10 mL) and water (50 mL)
  3. additionpotassium carbonate is added until the slurry
  4. additionThe slurry is diluted with water (50 mL)
  5. extractionthen extracted with methylene chloride (3×10 mL)
  6. dry with materialThe organic extracts are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e44bff48334342d98e29be8027762a8d
Source dataset
uspto-grants-2006_11
Patent number
US07135483B2

Reaction notes

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