Trifluoroacetic acid → 4-(4-Nitrophenoxy)piperidine

HRID 515262Notes

Reaction equation

HRID 515262 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].FC(F)(F)C(O)=O>ClCCl>[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 2794776Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate

Product 1

HCID 219186534-(4-Nitrophenoxy)piperidineYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate (3.10 mmol, 1 g) was dissolved in dichloromethane (10 mL). Trifluoroacetic acid (3 mL) was added and the reaction was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under vacuum and purified by SCX chromatography to afford the title compound (600 mg). MS (ESI) m/z 223.3 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by SCX chromatography

Sources & evidence

ORD record
ord-95065e5dea09490bb67de5a182be127c
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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