Trifluoroacetic acid → 3-(1-Pyrrolidinyl)-piperidine

HRID 341769Notes

Reaction equation

HRID 341769 reaction equation
C([O-])(=O)/C=C/C([O-])=O.C(OC([N:16]1[CH2:21][CH2:20][CH2:19][CH:18]([N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:17]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[N:22]1([CH:18]2[CH2:19][CH2:20][CH2:21][NH:16][CH2:17]2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 3984053-(1-Pyrrolidinyl)-1-piperidinecarboxylic acid 1,1-dimethylethyl esterHCID 5460307Fumarate

Product 1

HCID 5736113-(1-Pyrrolidinyl)-piperidineYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The fumarate of the title compound of Example 5 (2.00 g, 5.40 mmol) was suspended in CHCl3 (20 mL) and the solution was treated with CF3COOH (25 mL). TLC (solvent system A) indicated the reaction to be complete after 10 min at rt. The solvent was evaporated in vacuo and the residue was dissolved in cold (5° C.) 50% aqueous NaOH (100 mL) and extracted with CHCl3 (2×100 mL). The combined organic layer was dried (Na2SO4) and the solvent was evaporated in vacuo to give the title compound (0.80 g, quantitative) as a colorless oil. The HBr salt of the title compound crustallized from 2-propanol: mp 217°-218° C.; 1H-NMR (CDCl3) ∂ 3.22 (dm, Jgem +11 Hz, 1H), 2.94 (dm, Jgem +12 Hz, 1H), 2.48-2.62 (complex m, 6H), 1.98-2.11 (complex m, 2H), 1.65-1.82 (complex m, 6H), 1.30-1.54 (complex m, 2H); CIMS (calcd for C9H18N2): 155. Found (MH+): 155; Anal. (calcd for C9H20Br2N2): C, H, N.

Workup

  1. customthe reaction
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in cold (5° C.) 50% aqueous NaOH (100 mL)
  4. extractionextracted with CHCl3 (2×100 mL)
  5. dry with materialThe combined organic layer was dried (Na2SO4)
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-8cccf2c43b7d4348b3479be209d0a603
Source dataset
uspto-grants-1999_01
Patent number
US05856318

Reaction notes

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