Triphenylphosphine → 4-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3-chloronitrobenzene

HRID 1796196Notes

Reaction equation

HRID 1796196 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].[Cl:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1O.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:17]2[CH:18]=[CH:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][C:16]=2[Cl:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 12074NitrofunginHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 221810984-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3-chloronitrobenzeneYield 80.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 220568ethyl N-ethoxycarbonyliminocarbamateSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-4-hydroxypiperidine (3.32 g), 2-chloro-4-nitrophenol (2.36 g) and triphenylphosphine (5.11 g) in dichloromethane (60 ml), diethyl azodicarboxylate (3.10 ml) was added dropwise with stirring under ice-cooling, and the resulting mixture was stirred at room temperature for 18 hours and then evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (5:2) as the eluent to afford the title compound (3.90 g, yield: 76%) as a pale yellow solid.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature for 18 hours
  3. customevaporated in vacuo
  4. customThe residue obtained
  5. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-1e3a748eb73f4746ba9214dced3c8128
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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