Benzyl amide → HCID 14789753, compound

HRID 1886538Notes

Reaction equation

[F:1][C:2]1[C:3](=O)[C:4]2[C:12](=[C:13]([O:15][CH3:16])[CH:14]=1)[C:11]1[C:6](=[CH:7][C:8]([F:17])=[CH:9][CH:10]=1)[CH:5]=2.[CH2:19]([NH-:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]2[C:11]3[C:6](=[CH:7][C:8]([F:17])=[CH:9][CH:10]=3)[C:5](=[N:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 24 °C

Procedure

Titanium tetrachloride (0.127 mol, 127 mL of a 1.0 M methylene chloride solution) was added dropwise over a 15 minute to a mechanically stirred suspension of 2,7-difluoro-4-methoxyfluorenone (I) (50.0 g, 0.203 mol) and benzylamide (81 g, 0.76 mol) in methylene chloride (1 L) under nitrogen, keeping the temperature below 15° C. The mixture was stirred for 30 min while warming to 24° C., and then filtered through a pad of Florisil, washing with diethyl ether (4 L). The filtrate was concentrated to 500 mL and diluted with hexane (500 mL). The precipitated yellow imine was collected by filtration and combined with second and third crops obtained by concentration of the mother liquor to provide a total of 64 g (94%) of (II) as mixture of geometric isomers: IR (KBr) 1648, 1617, 1603, 1592, 1469, 1452, 1321, 1294 cm-1 ; 1H NMR (CDCl3, 200 MHz)δ7.95-6.40 (m, 10 H), 5.26 and 5.27 (singlets, total 2 H), 3.94 and 3.96 (singlets, total 6 H).

Workup

customthe temperature below 15° C
filtrationfiltered through a pad of Florisil
washwashing with diethyl ether (4 L)
concentrationThe filtrate was concentrated to 500 mL
additiondiluted with hexane (500 mL)
filtrationThe precipitated yellow imine was collected by filtration
customobtained by concentration of the mother liquor

Sources & evidence

ORD record: ord-fec9798972d440118f04df6d588eac4b
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05151544

Reaction notes

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