Hydrochloric Acid → HCID 21936777, compound

HRID 1242075Notes

Reaction equation

C(OC([N:8]1[CH2:17][CH2:16][C:11]2(OCC[O:12]2)[CH2:10][CH:9]1[CH2:18][N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:29])=O)(C)(C)C.Cl>FC(F)(F)C(O)=O.ClCCl>[O:12]=[C:11]1[CH2:16][CH2:17][NH:8][CH:9]([CH2:18][N:19]2[C:20](=[O:29])[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]2=[O:28])[CH2:10]1

Participants

Conditions

Temperature: 50 °C

Procedure

7-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (353 mg, 0.88 mmol) was cooled in an ice bath and then dissolved in a solution of 20% trifluoroacetic acid/dichloromethane (7 ml). The reaction was stirred for 5 minutes in the ice bath then another 3 hours at ambient temperature, after which it was concentrated in vacuo affording a solid residue. To the solid was added 2N hydrochloric acid (9 ml) and the mixture was heated at 50° C. (oil bath) with stirring for 24 h. The cooled reaction mixture was quenched with saturated sodium bicarbonate solution until the pH was basic. The aqueous layer was extracted with chloroform (3×20 ml) and the combined organic extracts dried (K2CO3), filtered, and the solvent evaporated in vacuo to give 205 mg (91%) of 2-(4-oxo-piperidin-2-ylmethyl)-isoindole-1,3-dione as a solid.

Workup

concentrationanother 3 hours at ambient temperature, after which it was concentrated in vacuo
customaffording a solid residue
customThe cooled reaction mixture
customwas quenched with saturated sodium bicarbonate solution until the pH
extractionThe aqueous layer was extracted with chloroform (3×20 ml)
dry with materialthe combined organic extracts dried (K2CO3)
filtrationfiltered
customthe solvent evaporated in vacuo

Sources & evidence

ORD record: ord-46f43199de764019831a2e6c63035d2c
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115624B1

Reaction notes

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