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 1353593Notes

Reaction equation

HRID 1353593 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-001ac72e1b594ffebe1b335c49ac9040
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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