Water → [4-(dimethylamino)phenyl][4-(9-H-thioxanthen-9-ylidene)-1-piperidinyl]methanone

To a magnetically stirred, ice-cooled solution of p-dimethylaminobenzoyl chloride (0.02 mole) and triethylamine (20 ml) in methylene chloride (300 ml) under an argon atmosphere was added dropwise a solution of 4-(9-thioxanthylidene)-piperidine (0.0133 mole) in methylene chloride (100 ml) over a twenty minute period. After stirring for 48 hours at room temperature, water (250 ml) was added and the mixture stirred for an additional 30 minutes. The layers were separated and the organic layer was washed with water (100 ml), 5% sodium hydroxide (2×200 ml) and water (250 ml), and then dried over sodium sulfate, filtered and stripped under reduced pressure to a dark orange oil. The product was purified by low pressure column chromatography using a 25×1000 mm column packed with 250 g. of silica gel absorbent and eluted with ethyl acetate to yield 2.3 grams of the product. Recrystallization from toluene yielded 2.1 g. of product, m.p. 178°-186° C. (decomp.)

1. stirringAfter stirring for 48 hours at room temperature
2. stirringthe mixture stirred for an additional 30 minutes
3. customThe layers were separated
4. washthe organic layer was washed with water (100 ml), 5% sodium hydroxide (2×200 ml) and water (250 ml)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customThe product was purified by low pressure column chromatography
8. washof silica gel absorbent and eluted with ethyl acetate

ORD-Eintrag

ord-63934fa7f6f64dd2a9ac27d6c7738c10

Quelldatensatz

uspto-grants-1982_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04356184