Trifluoroacetic acid → HCID 62475390, compound

HRID 1993661Notes

Reaction equation

HRID 1993661 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[C:27]([CH3:28])=[CH:26][C:25]([N+:29]([O-:31])=[O:30])=[CH:24][N:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[CH3:28][C:27]1[C:22]([O:21][CH:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)=[N:23][CH:24]=[C:25]([N+:29]([O-:31])=[O:30])[CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68538403HCID 68538403, compound

Product 1

HCID 62475390HCID 62475390, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

Add trifluoroacetic acid (150 mL) to a cold solution of 4-(3-methyl-5-nitro-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (10.12 g, 30 mmol) in dichloromethane (450 mL). Stir the reaction mixture at 22° C. for 60 min. After removal of solvent, treat the residue with 1 N sodium hydroxide (150 mL) and extract with dichloromethane and ethyl acetate. Dry the combined organic phases over sodium sulfate. Removal of solvent provides 3-methyl-5-nitro-2-(piperidin-4-yloxy)-pyridine as a yellow solid (6.9 g, 97% yield). MS(ES): m/z=238.2 [M+H].

Workup

  1. customAfter removal of solvent
  2. additiontreat the residue with 1 N sodium hydroxide (150 mL)
  3. extractionextract with dichloromethane and ethyl acetate
  4. dry with materialDry the combined organic phases over sodium sulfate
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-b9ed0c1968fd40049d87c1bfe9864a8d
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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