Trifluoroacetic acid → HCID 58739299, compound

HRID 720898Notes

Reaction equation

HRID 720898 reaction equation
C(O[C:6]([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:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:10][CH:9]1C)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:20]1([CH2:19][CH2:18][CH2:17][CH:16]([NH:15][C:14]([CH:11]2[CH2:12][CH2:13][N:8]([CH3:6])[CH2:9][CH2:10]2)=[O:35])[CH2:26][CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68573984HCID 68573984, compound

Product 1

HCID 58739299HCID 58739299, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[4-Phenyl-1-(3-phenyl-propyl)-butylcarbamoyl]-methylpiperidine-1-carboxylic acid tert-butyl ester (56) (1.62 g; 3.29 mmol) is dissolved in methylene chloride (50 mL) at ambient temperature. Trifluoroacetic acid (50 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 (30 mL) and water (200 mL), then potassium carbonate is added until the slurry is alkaline. The slurry is diluted with water (200 mL) then extracted with methylene chloride (3×100 mL). The organic extracts are dried over MgSO4, filtered, and concentrated in vacuo affording the desired product (1.23 g) as a white solid.

Workup

  1. concentrationThe solution is concentrated in vacuo at 40° C
  2. additionThe residue is slurried in a mixture of methylene chloride (30 mL) and water (200 mL)
  3. additionpotassium carbonate is added until the slurry
  4. additionThe slurry is diluted with water (200 mL)
  5. extractionthen extracted with methylene chloride (3×100 mL)
  6. dry with materialThe organic extracts are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da9e4bac93e74505994c5fb228aa4bc3
Source dataset
uspto-grants-2006_11
Patent number
US07135483B2

Reaction notes

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