Acetic Acid → HCID 13282023, compound

HRID 2295297Notes

Reaction equation

ClC([O:4][CH2:5][CH3:6])=O.[C:7](O)(=O)[CH3:8].[CH:11]1[S:12][CH:13]=[C:14]2[C:20]=1[C:19](=[O:21])[NH:18][C:17]1[CH:22]=[CH:23][CH:24]=[CH:25][C:16]=1[NH:15]2.[OH-].[Na+]>O1CCCC1>[CH3:16][N:15]1[CH2:8][CH2:7][CH:11]([CH2:6][C:5]([N:15]2[C:16]3[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=3[NH:18][C:19](=[O:21])[C:20]3=[CH:11][S:12][CH:13]=[C:14]23)=[O:4])[CH2:20][CH2:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

A quantity of 1.1 gm of ethyl chloroformate was added dropwise at 0° C. at a suspension of 1.57 gm (10 mmol) of 1-methyl-4-piperidinyl)acetic acid in 20 ml of tetrahydrofuran. Then, 2.16 gm (10 mmol) of 4,9-dihydro-10H-thieno-[3,4-b][1,5]benzodiazepin-10-one were added to the resulting suspension, which was then stirred for one hour at 0° C. and for a further four hours at ambient temperature. The suspension was then poured onto 160 ml of 2 N sodium hydroxide solution and extracted with toluene, and the organic phase was concentrated to dryness. After purification by column chromatography [silica gel; dioxane/methanol (1:1)], 4,9-dihydro-4-[(1-methyl-4-piperidinyl)-acetyl]-10H-thieno[3,4-b][1,5]benzodiazepin-10-one was obtained, m.p.: 184°-185° C. (ethyl acetate).

Workup

extractionextracted with toluene
concentrationthe organic phase was concentrated to dryness
customAfter purification by column chromatography [silica gel; dioxane/methanol (1:1)]

Sources & evidence

ORD record: ord-2fa7a2ef1cb04f0faae6be463af577f2
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04424225

Reaction notes

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