Water → HCID 49801353, compound

HRID 2193996Notes

Reaction equation

HRID 2193996 reaction equation
C([O:3][C:4]([C:6]1([CH2:22][CH2:23]OC)[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])(=[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>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:12]([N:9]1[CH2:8][CH2:7][C:6]2([C:4](=[O:3])[N:33]([C:32]3[CH:34]=[CH:35][C:29]([O:28][C:27]([F:36])([F:37])[F:26])=[CH:30][CH:31]=3)[CH2:23][CH2:22]2)[CH2:11][CH2:10]1)(=[O:14])=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 6008484-(Trifluoromethoxy)anilineHCID 16686359Dimethylalumanylium chlorideHCID 667876761-(2-Chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 49801353HCID 49801353, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8900HeptaneSolvent

Procedure

1-(2-chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.445 g) and 4-(trifluormethoxy)aniline (0.3 g) was dissolved in toluene (20 ml) under an argon atmosphere at RT, dimethylaluminium chloride in heptane (0.9 molar, 3.8 ml) was added and the mixture was refluxed for 3 hours. It was then cooled to RT, water (1 ml) was added and the reaction mixture was then stirred for 10 min. 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 8-(2-chloro-benzenesulfonyl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one as a white solid. MS (ESI): 489.08 (MH+).

Workup

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

Sources & evidence

ORD record
ord-cb6aa993afe145718d45b2f6389009b3
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

Loading…