Trifluoroacetic acid → 4-[4-(2-Oxazolin-2-yl)benzylidene]piperidine

HRID 129085Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:37]=[CH:36][C:9]([CH:10]=[C:11]2[CH2:16][CH2:15][N:14](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:13][CH2:12]2)=[CH:8][CH:7]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([CH:10]=[C:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)=[CH:36][CH:37]=1

Participants

Conditions

Temperature: -10 °C

Procedure

1.0 g of 4-[4-(2-oxazolin-2-yl) benzylidene]-1-tritylpiperidine in 20 ml of methylene chloride are treated slowly with 2 ml of trifluoroacetic acid at -10° C. After stirring for 1 hour at -10° C., the reaction mixture is poured into 150 ml of ice-water and immediately adjusted to pH 11.5 using 6N sodium hydroxide solution. After stirring for 10 minutes, it is extracted twice with 150 ml of ether, and the combined organic phases are washed, dried and evaporated down. The residue is purified by column chromatography on alumina (methylene chloride/methanol=40:1, v/v). 340 mg of the title compound of melting point 126° C. are obtained.

Workup

stirringAfter stirring for 10 minutes
extractionit is extracted twice with 150 ml of ether
washthe combined organic phases are washed
customdried
customevaporated down
customThe residue is purified by column chromatography on alumina (methylene chloride/methanol=40:1

Sources & evidence

ORD record: ord-e08a8e3c0c224281a94464db5b501dff
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05466687

Reaction notes

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