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4-(Trifluoromethoxy)aniline → 2-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-1,7-dione

HRID 420650
Notes
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Reaction equation

HRID 420650 reaction equation
C(O[C:4]([C:6]1([CH2:13][CH2:14]OC)[CH2:11][CH2:10][NH:9][C:8](=[O:12])[CH2:7]1)=[O:5])C.[F:17][C:18]([F:28])([F:27])[O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.[Cl-].C[Al+]C>C1(C)C=CC=CC=1.CCCCCC.CCOC(C)=O>[F:17][C:18]([F:27])([F:28])[O:19][C:20]1[CH:21]=[CH:22][C:23]([N:24]2[CH2:14][CH2:13][C:6]3([CH2:11][CH2:10][NH:9][C:8](=[O:12])[CH2:7]3)[C:4]2=[O:5])=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 6008484-(Trifluoromethoxy)anilineHCID 16686359Dimethylalumanylium chlorideHCID 584784144-(2-Methoxy-ethyl)-2-oxo-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 584784112-(4-Trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-1,7-dione

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent
HCID 8058
Hexane
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

4-(2-Methoxy-ethyl)-2-oxo-piperidine-4-carboxylic acid ethyl ester (2 g) and 4-(trifluormethoxy)aniline (3.09 g) were dissolved in toluene (100 ml) under an argon atmosphere at RT, dimethylaluminium chloride in hexane (1 molar, 39.25 ml) was added and the mixture was refluxed for 8 hours. The reaction mixture was then cooled to RT, diluted with AcOEt, quenched with water (9 ml), dried over MgSO4, filtered and the solvent was evaporated off. The residue was adsorbed on silica gel and purified by flash chromatography on silica gel (acetone/CH2Cl2, gradient from 0 to 40%) to give 2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decane-1,7-dione as light brown solid. MS (ESI): 329.1 (MH+).

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. customquenched with water (9 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was evaporated off
  6. custompurified by flash chromatography on silica gel (acetone/CH2Cl2, gradient from 0 to 40%)

Sources & evidence

ORD record
ord-716235da5c764bd5911ca7ef5b43de48
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08097634B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes