4-(Trifluoromethoxy)aniline → HCID 53233981, compound

HRID 1038994Notes

Reaction equation

HRID 1038994 reaction equation
C(O[C:4]([C:6]1([CH2:19][CH2:20]OC)[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])C.[F:23][C:24]([F:34])([F:33])[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.[Cl-].C[Al+]C>C1(C)C=CC=CC=1>[CH2:12]([N:9]1[CH2:8][CH2:7][C:6]2([C:4](=[O:5])[N:30]([C:29]3[CH:31]=[CH:32][C:26]([O:25][C:24]([F:23])([F:33])[F:34])=[CH:27][CH:28]=3)[CH2:20][CH2:19]2)[CH2:11][CH2:10]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6008484-(Trifluoromethoxy)anilineHCID 16686359Dimethylalumanylium chlorideHCID 66742460HCID 66742460, compound

Product 1

HCID 53233981HCID 53233981, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-benzyl-4-(2-methoxyethyl)-piperidine-4-carboxylic acid ethyl ester (5.2 g, 0.017 mol) and 4-(trifluormethoxy)aniline (4.57 ml, 0.034 mol) in toluene (200 ml) under an argon atmosphere at room temperature, was added dimethylaluminium chloride (0.9M solution in heptane, 37 ml, 0.034 mol) and the mixture was refluxed for 4 hours. The reaction mixture was cooled to room temperature and quenched was sat. Na2SO4(aq) solution and the mixture was filtered through Celite® and evaporated under reduced pressure. The crude residue was purified by flash column chromatography (1:3 AcOEt/heptane) to give 8-benzyl-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one as a white solid. MS (ESI): 405.4 (MH+).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customquenched
  3. filtrationthe mixture was filtered through Celite®
  4. customevaporated under reduced pressure
  5. customThe crude residue was purified by flash column chromatography (1:3 AcOEt/heptane)

Sources & evidence

ORD record
ord-6e038a4c573e4637aaa3dadbdf733f6c
Source dataset
uspto-grants-2013_10
Patent number
US08552024B2

Reaction notes

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