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

HRID 2250242Notes

Reaction equation

HRID 2250242 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][NH:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.[S:23](N)(N)(=[O:25])=[O:24].Cl.C(OCC)C>N1C=CC=CC=1.C(OCC)(=O)C.O1CCOCC1>[CH2:12]([N:9]1[CH2:10][CH2:11][CH:6]([N:5]2[CH2:4][C:3]3[CH:19]=[CH:20][CH:21]=[CH:22][C:2]=3[NH:1][S:23]2(=[O:25])=[O:24])[CH2:7][CH2:8]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 82267SulfamideHCID 13051020N-((2-aminophenyl)methyl)-1-benzylpiperidin-4-amine

Product 1

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

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (2-amino-benzyl)-(1-benzyl-piperidin-4-yl)-amine (1.0 g, 3.39 mmol) and sulfamide (0.64 g, 6.78 mmol) in pyridine was heated at reflux for 14 h. After cooling to room temperature, the solvent was evaporated and the crude product dissolved in water. After being adjusted to pH 9 with 6N sodium hydroxide, the resulting mixture was extracted with methylene chloride (2×). The extracts were washed with water (2×), dried over sodium sulfate, filtered, and concentrated to afford an oily residue which was dissolved in ethyl acetate (4 mL). This solution was mixed with 4N HCl in 1,4-dioxane (2 mL) followed by addition of diethyl ether until precipitation of product occurred. The desired product was obtained by filtration to afford 0.7 g (53%). LC/MS: tR=0.96 min, 358.16 (MH)+.

Workup

  1. temperatureat reflux for 14 h
  2. customthe solvent was evaporated
  3. dissolutionthe crude product dissolved in water
  4. extractionthe resulting mixture was extracted with methylene chloride (2×)
  5. washThe extracts were washed with water (2×)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford an oily residue which

Sources & evidence

ORD record
ord-1d1c4f0009244fecb3d25b8fd7b79c56
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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