Triphenylphosphine → HCID 53908672, compound

HRID 458870Notes

Reaction equation

O[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:16])[CH:8]=[CH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:36]1([CH:42]2[CH2:47][C:46](=[O:48])[NH:45][C:44](=[O:49])[CH2:43]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[O:48]=[C:46]1[CH2:47][CH:42]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:43][C:44](=[O:49])[N:45]1[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:16])[CH:8]=[CH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 15 °C

Procedure

9.3 g (42.3 mmol) N-(4-hydroxy-butyl)-3-pyridin-3-yl-acrylamide, 11.1 g (42.3 mmol) triphenylphosphine and 8.0 g (42.3 mmol) 4-phenyl-piperidin-2,6-dione are suspended in 120 ml THF, thereafter 6.7 ml (42.3 mmol) azodicarboxylic acid diethyl ester dissolved in 60 ml THF are added dropwise within three hours under protective atmosphere and light cooling (to ca. 15° C.). The mixture is left standing overnight without further cooling at RT. Subsequently, the solvent is removed under vacuum and the residue is chromatographically purified over silica gel with CHCl3/CH3OH (95/5) and, after withdraw of the solvent, crystallized from acetic acid ethyl ester: Colorless crystals with MP. 160–161° C.; Yield 3.8 g (23%).

Workup

additionare added dropwise within three hours under protective atmosphere and light
waitThe mixture is left
temperaturewithout further cooling at RT
customSubsequently, the solvent is removed under vacuum
customthe residue is chromatographically purified over silica gel with CHCl3/CH3OH (95/5)
customafter withdraw of the solvent
customcrystallized from acetic acid ethyl ester
customwith MP. 160–161° C.

Sources & evidence

ORD record: ord-b43c55d4f28a4d34be71d5cec2e29c38
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192967B1

Reaction notes

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