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

HRID 1280781Notes

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-diphenylmethylpiperidin-4-yl)-butan-1-ol, 109.5 g (417 mmol) triphenylphosphine and 61.3 g (417 mmol) phthalimide are suspended in THF and 72.6 g (417 mmol) azodicarboxylic acid diethyl ester are added dropwise within 2½ hours under protective atmosphere and light cooling (ca. 15-25° C.). After a further hour, the solvent is removed under vacuum and the residue is crystallized three times from acetic acid ester (1000 ml, 1200 ml and 1100 ml). Colorless crystals with a MP of 150-152 were recovered. Yield 103 g (54.5%).

Workup

waitAfter a further hour
customthe solvent is removed under vacuum
customthe residue is crystallized three times from acetic acid ester (1000 ml, 1200 ml and 1100 ml)
customColorless crystals with a MP of 150-152 were recovered

Sources & evidence

ORD record: ord-d2844f0bd98644a6a8ecf2c25df290a8
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451816B1

Reaction notes

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