Phthalimide → HCID 69304319, compound

HRID 1927626Notes

Reaction equation

HRID 1927626 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4](=[O:27])[CH:5]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][C:19]=2[F:26])[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:49]1(=[O:59])[NH:53][C:52](=[O:54])[C:51]2=[CH:55][CH:56]=[CH:57][CH:58]=[C:50]12.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:54]=[C:52]1[C:51]2[C:50](=[CH:58][CH:57]=[CH:56][CH:55]=2)[C:49](=[O:59])[N:53]1[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([N:15]2[CH2:14][CH2:13][N:12]([CH:5]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:4]([N:3]([CH2:28][CH3:29])[CH2:1][CH3:2])=[O:27])[CH2:17][CH2:16]2)=[C:19]([F:26])[CH:20]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 69304083N,N-Diethyl-2-[4-(2-fluoro-4-hydroxymethyl-phenyl)-piperazin-1-yl]-2-phenyl-acetamide

Product 1

HCID 69304319HCID 69304319, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N,N-diethyl-2-[4-(2-fluoro-4-hydroxymethyl-phenyl)-piperazin-1-yl]-2-phenyl-acetamide (0.14 g, 0.362 mmol) in THF (3 mL) was added triphenylphosphine (96.5 mg), phthalimide (76.9 mg), and diethyl azodicarboxylate (50 μL), and the mixture stirred at rt. After 16 h, the solvent was removed and the residue purified on SiO2EtOAc/hexanes) to provide 115.5 mg of the title compound. MS (ESI): mass calcd. for C31H33FN4O3, 528.62. m/z found, 529.6 [M+H]+.

Workup

  1. customthe solvent was removed
  2. customthe residue purified on SiO2EtOAc/hexanes)

Sources & evidence

ORD record
ord-096015c799d04ce199fd8500daf09185
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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