Phthalimide → 2-[4-(1-Diphenylmethylpiperidin-4-yl)-butyl]-isoindol-1,3-dione

HRID 1278971Notes

Reaction equation

[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17]O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:44]1(=[O:54])[NH:48][C:47](=[O:49])[C:46]2=[CH:50][CH:51]=[CH:52][CH:53]=[C:45]12.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:48]3[C:44](=[O:54])[C:45]4[C:46](=[CH:50][CH:51]=[CH:52][CH:53]=4)[C:47]3=[O:49])[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 20 °C

Procedure

135.0 g (417. mmol) 4-(1-diphenylmethyl-piperidin-4-yl)-butan-1-ol, 109.5 g (417 mmol) triphenylphosphine and 61.3 g (417 mmol) phthalimide are suspended in THF. Thereafter, 2.6 g (417 mmol) azodicarboxylic acid diethyl ester are added dropwise within two and a half hours under protective atmosphere and light cooling (ca. 15-25° C.). After an additional hour, the solvent is removed under vacuum and the residue is crystallized three times from acetic acid ethyl ester (1000 ml, 1200 ml and 1100 ml). Colorless crystals with an MP of 150-152° C.; yield 103 g (54.5 %).

Workup

waitAfter an additional hour
customthe solvent is removed under vacuum
customthe residue is crystallized three times from acetic acid ethyl ester (1000 ml, 1200 ml and 1100 ml)

Sources & evidence

ORD record: ord-55061712b5e04678bb0ae35a6ecd2898
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444823B1

Reaction notes

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