Triphenylphosphine → HCID 67067066, compound

HRID 2074321Notes

Reaction equation

HRID 2074321 reaction equation
[OH:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[O:15])[CH2:10][CH2:9]2)=O)=[CH:4][CH:3]=1.N(C(OCC)=O)=NC(OCC)=O.[Cl:37][C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=1)[CH2:41][OH:42].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl.C1COCC1>[Cl:37][C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=1)[C:41]([O:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)=[O:42]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 701173-Chlorobenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67067074HCID 67067074, compound

Product 1

HCID 67067066HCID 67067066, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A THF (5 ml) solution containing 3-pyridyl 4-(4-hydroxybenzoyl)-1-piperazinecarboxylate (300 mg) and diethyl azodicarboxylate (0.62 ml, 40% Tol solution) was dropwise added to a THF (5 ml) solution containing 3-chlorobenzyl alcohol (200 mg) and triphenylphosphine (360 mg), at 0° C., followed by stirring at room temperature for 3 days. The reaction solution was diluted with chloroform, washed with an aqueous saturated sodium hydrogencarbonate solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform:methanol=95:5 (v/v)), and the resulting solid was recrystallized from 2-propanol to obtain 3-pyridyl 4-{4-[(3-chlorobenzoyl)oxy]benzyl}-1-piperazinecarboxylate (260 mg).

Workup

  1. customat 0° C.
  2. washwashed with an aqueous saturated sodium hydrogencarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: chloroform:methanol=95:5 (v/v))
  6. customthe resulting solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-681dae90b3d34b0981af07ef97542eb5
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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