Trifluoroacetic acid → HCID 68552816, compound

HRID 1804848Notes

Reaction equation

HRID 1804848 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([O:16]C(C)(C)C)=[O:15])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:21][CH3:22].FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:21][CH3:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68553903HCID 68553903, compound

Product 1

HCID 68552816HCID 68552816, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 1-(4-chloro-3-methoxyphenyl)piperidine-4-carboxylate (0.500 g, 1.535 mmol; this starting material was isolated as a reaction product in Example 1a, Step 1) in anhydrous CH2Cl2 (5 mL) was treated with trifluoroacetic acid (3 mL, 38.9 mmol) and the mixture stirred at RT for 2 h. After this time, the mixture was concentrated on the a rotary evaporator and the resultant residue was neutralized by first treating it with 2 M NaOH and then 0.1 M pH 7 phosphate buffer. The resultant mixture was extracted with EtOAc, and the extract was washed with brine, dried (MgSO4) and concentrated to give 1-(4-chloro-3-methoxyphenyl)piperidine-4-carboxylic acid (0.45 g, 1.668 mmol, >100% yield) as a pale yellow solid. LC-MS: 270, [M+H].

Workup

  1. concentrationAfter this time, the mixture was concentrated on the a rotary evaporator
  2. additionby first treating it with 2 M NaOH
  3. extractionThe resultant mixture was extracted with EtOAc
  4. washthe extract was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a1cdd3a751cb4c119f47cbdf03134335
Source dataset
uspto-grants-2013_01
Patent number
US08354432B2

Reaction notes

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