4-Phenylpiperidine → N-(1-Benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-(4-phenyl-piperidin-1-yl)-benzenesulfonamide

HRID 1716272Notes

Reaction equation

HRID 1716272 reaction equation
[CH2:1]([O:8][N:9]1[CH2:15][CH:14]=[CH:13][CH2:12][C@@H:11]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:10]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]1([CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CS(C)=O>[CH2:1]([O:8][N:9]1[CH2:15][CH:14]=[CH:13][CH2:12][C@@H:11]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([N:37]3[CH2:38][CH2:39][CH:34]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:35][CH2:36]3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:10]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 698734-PhenylpiperidineHCID 68516333N-(1-Benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-fluoro-benzenesulfonamide

Product 1

HCID 68514537N-(1-Benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-(4-phenyl-piperidin-1-yl)-benzenesulfonamideYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 100 mg of N-(1-benzyloxy-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-(R)-yl)-4-fluoro-benzenesulfonamide from Step A in 2 mL of methylsulfoxide was added 100 mg of 4-phenyl piperidine. The solution was heated to 70° C. for 5 days. The reaction was cooled, and the mixture extracted with ethyl acetate. The organic layers were washed twice with NaCl(aq.) solution, followed by drying over Na2SO4(s). Filtration, solvent removal, was followed by dilution with ethyl ether. Filtration of the resulting solids, washing with ethyl ether and methanol, and drying gave 83 mg of an off-white solid. MS: 1063 (2M+H), 532 (M+H).

Workup

  1. temperatureThe reaction was cooled
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe organic layers were washed twice with NaCl(aq.) solution
  4. dry with materialby drying over Na2SO4(s)
  5. filtrationFiltration, solvent removal
  6. filtrationFiltration of the resulting solids
  7. washwashing with ethyl ether and methanol
  8. customdrying

Sources & evidence

ORD record
ord-3c58b666d92040938464c89ee071efb1
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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