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Triphenylphosphine → HCID 19802562, compound

HRID 1645817
Notes
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Reaction equation

HRID 1645817 reaction equation
O[CH:2]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH2:6][CH2:5]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1.CCOC(/N=N/C(OCC)=O)=O>ClCCl>[CH3:17][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH:2]([N:43]2[CH2:47][CH2:46][CH2:45][CH2:44]2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:5][CH2:6]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 31268PyrrolidineHCID 5462977Diethyl azodicarboxylateHCID 163323132-[4-(2-methoxyphenyl)piperazin-1-yl]-1-phenylethanol

Product 1

HCID 19802562HCID 19802562, compound

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Conditions

Temperature
0.5 °C

Procedure

A mixture of 1-(2-hydroxy-2-phenylethyl)-4-(2-methoxyphenyl)-piperazine (5.65 g; 0.018 m), triphenylphosphine (5.69 g, 0.022m) and pyrollidine (15 ml; 0.18 m) in dichloromethane (100 ml) was stirred at 0.5° C. and a solution of diethylazodicarboxylate (3.8 ml, 0.024 m) in dichloromethane (5 ml) was added over 5 minutes. The resulting yellow solution was stirred at ambient temperature for 48 hrs. The residue on evaporation was partitioned between ether and 3N aq. hydrochloric acid. The combined HCl layers were washed with ether and then basified with ammonia and shaken with 3 portions of ether. The ether layers were washed well with water and dried over magnesium sulfate to give an oil which was chromatographed to give 0.96 g of the title compound. The crude oil in ethanol was acidified with ethanolic hydrogen chloride. The solvent was evaporated, and the residual foam solidified when triturated with ethanol and ether. The solid was recrystallised from ethanol to give the title compound as the dihydrochloride (0.45 g), m.p. 214°-18° C(d).

Workup

  1. stirringThe resulting yellow solution was stirred at ambient temperature for 48 hrs
  2. customThe residue on evaporation
  3. customwas partitioned between ether and 3N aq. hydrochloric acid
  4. washThe combined HCl layers were washed with ether
  5. stirringshaken with 3 portions of ether
  6. washThe ether layers were washed well with water
  7. dry with materialdried over magnesium sulfate
  8. customto give an oil which
  9. customwas chromatographed

Sources & evidence

ORD record
ord-e467bae9c7c7407b90d2a6935574e9cb
Source dataset
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05177078

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes