Water → benzyl 2'-oxo-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]-1-carboxylate

HRID 1695911Notes

Reaction equation

ClC1N=C(Cl)N=C(Cl)N=1.O[N:11]=[C:12]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:14]2([CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:16][CH2:15]2)[CH2:13]1.[OH2:36]>CN(C=O)C>[O:36]=[C:12]1[CH2:13][C:14]2([CH2:15][CH2:16][N:17]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH2:18][CH2:19]2)[C:30]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:11]1

Participants

Conditions

Temperature: 25 °C

Procedure

2,4,6-trichloro-[1,3,5]-triazine (1.32 g, 7.16 mmol) was added to DMF (9.6 mL) maintained at 25° C. The reaction was monitored by TLC until TCT was consumed. Then benzyl 3-(hydroxyimino)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (1.6 g, 4.77 mmol) in DMF (17 mL) was added. After the addition, the mixture was stirred at room temperature overnight. Water was added. The mixture was extracted with EtOAc. The combined organic layers were washed with sat. Na2CO3, followed by 1N HCl and brine, dried over Na2SO4 and concentrated. The residue was purified by prep HPLC to obtain benzyl 2′-oxo-2′,3′-dihydro-1′H-spiro[piperidine-4,4′-quinoline]-1-carboxylate (260 mg, yield 16%).

Workup

customwas consumed
additionAfter the addition
extractionThe mixture was extracted with EtOAc
washThe combined organic layers were washed with sat. Na2CO3
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified by prep HPLC

Sources & evidence

ORD record: ord-27cd934a0a964a6a9e54a6ab2dbb7467
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163737B2

Reaction notes

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