Potassium Carbonate → HCID 19788729, compound

HRID 1656601Notes

Reaction equation

HRID 1656601 reaction equation
Cl.[CH3:2][S:3]([NH:6][C:7]1[CH:20]=[CH:19][C:10]([C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)(=[O:5])=[O:4].[C:21]([O-:24])([O-])=O.[K+].[K+]>C(O)C>[OH:12][CH:11]([CH2:13][N:16]1[CH2:17][CH2:18][CH:13]([C:11](=[O:12])[C:10]2[CH:9]=[CH:8][C:7]([NH:6][S:3]([CH3:2])(=[O:4])=[O:5])=[CH:20][CH:19]=2)[CH2:14][CH2:15]1)[CH2:10][O:24][C:21]1[CH:19]=[CH:20][C:7]([NH:6][S:3]([CH3:2])(=[O:5])=[O:4])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 14130042N-[4-(piperidine-4-carbonyl)-phenyl]methanesulfonamide hydrochloride

Product 1

HCID 19788729HCID 19788729, compoundYield 155.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 4-[4-methylsulfonylaminobenzoyl)piperidine hydrochloride (2.25 g, 7.06 mmol), 2-[(4-(methylsulfonyamino)phenoxy)-methyl]oxirane (U.S. Pat. No. 4,994,459, 1.73 g, 7.06 mmol) and K2CO3 (0.98 g, 7.06 mmol) in ethanol (40 mL) was heated at 90° C. for 24 hours and then at 25° C. for an additional 24 hours. The mixture was concentrated and the residue was partitioned between aqueous 10% NaHCO3 and 4:1 CH2Cl2 /isopropanol. The organic phase was dried and concentrated to afford 2.89 g (78%) of the title compound. A portion (1.60 g) was purified by HPLC (15% CH3OH/EtOAc) to give 0.92 g of product as a white solid: mp 179°-183° C. (dec); 1H NMR (DMSO-d6): δ 10.20 (brs, 1H), 9.33 (brs, 1H), 7.94 (d, J=8.72 Hz, 2H), 7.26 (d, J=8.92 Hz, 2H), 7.13 (d, J=9.13 Hz, 2H), 6.91 (d, J=8.92 Hz, 2H), 4.83 (m,1H), 3.93 (m, 2H), 3.85 (m, 1H), 3.09 (s, 3H), 2.96 (m, 2H), 2.87 (s, 3H), 2.45 (m, 2H), 2.20 (m, 2H), 1.75-1.50 (m, 4H); IR (KBr): 3420, 3300, 3250, 2910, 1675, 1610 cm-1 ; MS (m/z) 526 (MH+, 25%), 217 (40), 91 (100).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between aqueous 10% NaHCO3 and 4:1 CH2Cl2 /isopropanol
  3. customThe organic phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9df676035f054f62bfe073a89fc89353
Source dataset
uspto-grants-1993_10
Patent number
US05254689

Reaction notes

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