Phthalimide → 2-(4-{1-[bis(4-Fluorophenyl)-methyl]-piperidin-4-yl}-butyl)-isoindol-1,3-dione

HRID 1280772Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18]O)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:46]1(=[O:56])[NH:50][C:49](=[O:51])[C:48]2=[CH:52][CH:53]=[CH:54][CH:55]=[C:47]12.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][N:50]3[C:46](=[O:56])[C:47]4[C:48](=[CH:52][CH:53]=[CH:54][CH:55]=4)[C:49]3=[O:51])[CH2:11][CH2:10]2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 20 °C

Procedure

23.1 g (62.5 mmol) 4-{1-[bis(4-fluorophenyl)-methyl]-piperidin-4-yl}-butan-1-ol, 16.4 g (62.5 mmol) triphenylphosphine and 9.2 g (62.5 mmol) phthalimide are suspended in THF and 10.9 g (62.5 mmol) azodicarboxylic acid diethyl ester is added dropwise under a protective atmosphere and light cooling (ca. 15-25° C.). The mixture is stirred for three hours at RT and subsequently the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CH2Cl2/CH3OH (99.5/0.5) Yield: 27.6 g (90%).

Workup

customsubsequently the solvent is removed under vacuum
customThe residue is chromatographically purified over silica gel with CH2Cl2/CH3OH (99.5/0.5) Yield: 27.6 g (90%)

Sources & evidence

ORD record: ord-85a2ace78a804e8d96b06fd3042bbe09
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451816B1

Reaction notes

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