Ethylamine → HCID 15551259, compound

HRID 379705Notes

Reaction equation

C1(C)C=CC(S(O[CH2:11][CH2:12][O:13][C:14]2[CH:28]=[CH:27][C:17]([NH:18][C:19]([CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:20])=[CH:16][CH:15]=2)(=O)=O)=CC=1.[CH2:30]([NH2:32])[CH3:31]>O1CCOCC1>[CH2:30]([NH:32][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([NH:18][C:19]([CH:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[O:20])=[CH:27][CH:28]=1)[CH3:31]

Participants

Conditions

Temperature: 90 °C

Procedure

4′-[2-(p-Toluenesulfonyloxy)ethoxy]-3,4,5,6-tetrahydro-2H-pyran-4-carboxanilide (1.7 g) solution in dioxane (20 ml) was added with 70% ethylamine aqueous solution (1.63 ml) and stirred for 6 hours at 90° C. The reaction mixture was concentrated under vacuum and dissolved into 2N HCl (20 ml). This solution was washed with ethyl acetate (20 ml) two times. Aqueous layer was neutralized with 2N sodium hydroxide (20 ml). Solid formed was extracted with ethyl acetate (50 ml), washed with water and then dehydrated with anhydrous magnesium sulfate. After filtration, filtrate was concentrated under vacuum and purified with silica-gel column chromatography to obtain 4′-[2-(ethylamino)ethoxy]-3,4,5,6-tetrahydro-2H-pyran-4-carboxanilide (0.77 g) as white solid.

Workup

concentrationThe reaction mixture was concentrated under vacuum
dissolutiondissolved into 2N HCl (20 ml)
washThis solution was washed with ethyl acetate (20 ml) two times
customSolid formed
extractionwas extracted with ethyl acetate (50 ml)
washwashed with water
filtrationAfter filtration, filtrate
concentrationwas concentrated under vacuum
custompurified with silica-gel column chromatography

Sources & evidence

ORD record: ord-ce60293a377d423da99766a6144b374d
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300368B1

Reaction notes

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