m-(Trifluoromethyl)nitrobenzene → Tert-butyl 4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate

HRID 1796206Notes

Reaction equation

HRID 1796206 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]([F:28])([F:27])[C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1O.FC(F)(F)C1C=C([N+]([O-])=O)C=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.N(C(OCC)=O)=NC(OCC)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:18]2[CH:19]=[CH:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][C:17]=2[C:16]([F:15])([F:27])[F:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 7386m-(Trifluoromethyl)nitrobenzeneHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 3014014Phenol, 4-nitro-2-(trifluoromethyl)-

Product 1

HCID 22181018Tert-butyl 4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 220568ethyl N-ethoxycarbonyliminocarbamateSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (1.45 g), 2-trifluoromethyl-4-nitrophenol (1.38 g), which was prepared from 3-trifluoromethylnitrobenzene according to the method described in J. Org. Chem., 63, 4199 (1998), and triphenylphosphine (2.27 g) in dichloromethane (65 ml), diethyl azodicarboxylate (1.4 ml) was added dropwise with stirring under ice-cooling, and the resulting mixture was stirred at room temperature overnight and then evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using dichloromethane as the eluent to afford the title compound (2.28 g, yield: 88%) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. customevaporated in vacuo
  4. customThe residue obtained
  5. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-2c2b93391aae4db1b0cec91fb04f56ba
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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