Trifluoroacetic acid → 2-(Piperidin-4-yl)acetonitrile

HRID 604312Notes

Reaction equation

HRID 604312 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]#[N:23])[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]#[N:23])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22248390tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylate

Product 1

HCID 100119032-(Piperidin-4-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (23 mL, 34.7 g, 304 mmol) to 4-cyanomethylpiperidine-1-carboxylic acid t-butyl ester (5.43 g, 24.21 mmol) in DCM (25 mL) and stir at room temperature for 18 hr. Remove the solvent in vacuo and dissolve in methanol (50 mL) and pour onto an SCX-2 column. Elute with 2 M ammonia in methanol and evaporate the eluent to give piperidin-4-ylacetonitrile as an oil which solidifies on standing (2.78 g, 92%). MS (m/z): 125.1 (M+1).

Workup

  1. customRemove the solvent in vacuo
  2. dissolutiondissolve in methanol (50 mL)
  3. additionpour onto an SCX-2 column
  4. washElute with 2 M ammonia in methanol
  5. customevaporate the eluent

Sources & evidence

ORD record
ord-e35b087a342a4f1c8d6406b136ff8b5f
Source dataset
uspto-grants-2011_03
Patent number
US07910588B2

Reaction notes

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