Triphenylphosphine → HCID 18318231, compound

HRID 1700290Notes

Reaction equation

HRID 1700290 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[O:10])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:38]1[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:47]([O:46][C:44]([N:41]1[CH2:42][CH2:43][CH:38]([O:1][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[O:10])=[CH:4][C:3]=2[N+:15]([O-:17])=[O:16])[CH2:39][CH2:40]1)=[O:45])([CH3:50])([CH3:48])[CH3:49]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 18318131HCID 18318131, compound

Product 1

HCID 18318231HCID 18318231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-hydroxy-3-nitro-N-(trifluoromethylcarbonyl)benzenamine (10.0 g), triphenylphosphine (22.1 g) and 4-hydroxy-N-(t-butoxycarbonyl)piperidine (17.0 g) in THF (30 mL) was added DEAD (13.5 mL) drop-wise. The reaction was stirred at ambient temperature for 1 hour, concentrated and purified on silica gel column (ethyl acetate/hexane, gradient) to afford 4-(N′-(t-butoxycarbonyl)piperidin-4-yl)oxy-3-nitro-N-(trifluoromethylcarbonyl)benzenamine.

Workup

  1. concentrationconcentrated
  2. custompurified on silica gel column (ethyl acetate/hexane, gradient)

Sources & evidence

ORD record
ord-125e52dfcfb74f088407658ced17373e
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

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