Water → HCID 49801654, compound

HRID 2194004Notes

Reaction equation

HRID 2194004 reaction equation
C([O:3][C:4]([C:6]1([CH2:21][CH2:22][CH2:23]OC)[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1)=O)C.[F:26][C:27]([F:37])([F:36])[O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1.[Cl-].C[Al+]C.O>C1(C)C=CC=CC=1.CCCCCCC>[C:15]1([S:12]([N:9]2[CH2:8][CH2:7][C:6]3([C:4](=[O:3])[N:33]([C:32]4[CH:34]=[CH:35][C:29]([O:28][C:27]([F:36])([F:37])[F:26])=[CH:30][CH:31]=4)[CH2:23][CH2:22][CH2:21]3)[CH2:11][CH2:10]2)(=[O:13])=[O:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6008484-(Trifluoromethoxy)aniline2×HCID 16686359Dimethylalumanylium chloride2×HCID 66787540HCID 66787540, compound

Product 1

HCID 49801654HCID 49801654, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8900HeptaneSolvent2×

Procedure

1-Benzenesulfonyl-4-(3-methoxy-propyl)-piperidine-4-carboxylic acid ethyl ester (0.3 g) was dissolved under an argon atmosphere in toluene (10 ml), 4-(trifluormethoxy)-aniline (0.173 g) was added followed by dimethylaluminium chloride in heptane (1.8 ml, 0.9 molar). The mixture was refluxed 3 hours, more 4-(trifluormethoxy)-aniline (0.173 g) and dimethylaluminium chloride in heptane (1.8 ml) were added and refluxing was continued for further 3 hours. The reaction mixture was then cooled to RT, water (1 ml) was added and the mixture was stirred for 10 minutes. The solvent was evaporated off, the residue absorbed on silica gel and purified by flash-chromatography (AcOEt/heptane, gradient from 0 to 25%) to give the desired 9-benzenesulfonyl-2-(4-trifluoromethoxy-phenyl)-2,9-diaza-spiro[5.5]undecan-1-one (0.215 g) as a white solid. MS (ESI): 469.13 (MH+)

Workup

  1. temperatureThe mixture was refluxed 3 hours
  2. temperaturerefluxing
  3. customThe solvent was evaporated off
  4. customthe residue absorbed on silica gel
  5. custompurified by flash-chromatography (AcOEt/heptane, gradient from 0 to 25%)

Sources & evidence

ORD record
ord-d1fcd195c5d94106847f6740e37c1597
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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