Triphenylphosphine → HCID 22154693, compound

HRID 1708887Notes

Reaction equation

HRID 1708887 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[F:13][C:14]1[C:19]([F:20])=[CH:18][C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:15]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:44]([N:51]1[CH2:56][CH2:55][N:54]([CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[CH2:53][CH:52]1[CH2:64][OH:65])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1COCC1>[CH2:44]([N:51]1[CH2:56][CH2:55][N:54]([CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[CH2:53][CH:52]1[CH2:64][O:65][C:18]1[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][CH:15]=[C:14]([F:13])[C:19]=1[F:20])[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10827800(1,4-Dibenzylpiperazin-2-yl)methanolHCID 221546562,3-Difluoro-5-nitrophenol

Product 1

HCID 22154693HCID 22154693, compoundYield 6,043.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(1Ba) A solution of 4.7 g (27 mmol) of diethyl azodicarboxylate in 15 ml of THF was added dropwise at 15° C. while stirring to a solution of 3.9 g (22.5 mmol) of 2,3-difluoro-5-nitrophenol, 7.1 g (27 mmol) of triphenylphosphine and 8 g (0.27 mmol) of 1,4-dibenzyl-2-hydroxymethylpiperazine in 250 ml of THF. The yellow reaction solution was then stirred at room temperature for an additional 3 hours. After concentrating the reaction solution, the oily residue was stirred with a total of 2 l of hot n-hexane in several portions. The hexane solution was separated and cooled. The separated triphenylphosphine oxide was removed by filtration under suction, and the filtrate was concentrated. Chromatography on silica gel with ether/n-hexane (1:1) as the eluent gave 7.4 g of 1,4-dibenzyl-2-[(6-nitro-2,3-difluorophenoxy)methyl]-piperazine as a brown oil.

Workup

  1. concentrationAfter concentrating the reaction solution
  2. stirringthe oily residue was stirred with a total of 2 l of hot n-hexane in several portions
  3. customThe hexane solution was separated
  4. temperaturecooled
  5. customThe separated triphenylphosphine oxide was removed by filtration under suction
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-024405a648a94e6d80922e52eacad7d1
Source dataset
uspto-grants-1990_08
Patent number
US04946847

Reaction notes

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