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

HRID 1695911
Notes
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Reaction equation

HRID 1695911 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 7954Cyanuric chlorideHCID 72297710Benzyl 3-(hydroxyimino)-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

Product 1

HCID 59433237benzyl 2'-oxo-2',3'-dihydro-1'H-spiro[piperidine-4,4'-quinoline]-1-carboxylateYield 16%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent
2×

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

  1. customwas consumed
  2. additionAfter the addition
  3. extractionThe mixture was extracted with EtOAc
  4. washThe combined organic layers were washed with sat. Na2CO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes