3-(1-benzylpiperidin-4-yl)-3,4-dihydro-1H-2$l^{6},1,3-benzothiadiazine-2,2-dione → 3-(piperidin-4-yl)-3,4-dihydro-1H-benzo[c][1,2,6]thiadiazine 2,2-dioxide

HRID 2250243Notes

Reaction equation

HRID 2250243 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[NH:16][S:15]2(=[O:25])=[O:24])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[NH:16][S:15]2(=[O:25])=[O:24])[CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 131172113-(1-benzylpiperidin-4-yl)-3,4-dihydro-1H-2$l^{6},1,3-benzothiadiazine-2,2-dione

Product 1

HCID 131172133-(piperidin-4-yl)-3,4-dihydro-1H-benzo[c][1,2,6]thiadiazine 2,2-dioxideYield 75.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(1-Benzyl-piperidin-4-yl)-3,4-dihydro-1H-benzo[1,2,6]thiadiazine-2,2-dioxide (0.46 g, 1.29 mmol) in methanol (10 mL) was flushed with nitrogen, and treated with palladium on charcoal (10%, 46 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Column chromatography gave 0.26 g (75%) of the desired material. 1H-NMR (CD3OD) δ 1.53-1.61 (m, 2H), 1.80 (m, 2H), 2.55 (m, 2H), 2.95-3.05 (m, 2H), 3.30 (m, 2H), 3.70 (m, 2H), 4.65 (s, 2H), 6.70 (d, J=7.9, 1H), 7.40 (dd, J=8.2, 6.7, 1H), 7.10 (m, 2H). Mass spec.: 268.10 (MH)+.

Workup

  1. customThe flask was flushed with hydrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cfe308c042f54b33816fc0243d6edf07
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

Loading…