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

HRID 1782708Notes

Reaction equation

HRID 1782708 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1.[S:23](N)(N)(=[O:25])=[O:24]>N1C=CC=CC=1>[O:24]=[S:23]1(=[O:25])[N:9]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:14][CH2:15]2)[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1]1

Participants

4

Reactant 2

HCID 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 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 11.0 g (0.0372 mol) of 2-amino-N-[1-(phenylmethyl)-4-piperidinyl]-benzenemethanamine in 200 ml of pyridine was added dropwise within 1.5 hours and at reflux temperature to a solution of 3.4 g (0.0354 mol) of sulphamide in 200 ml of pyridine and the mixture was then refluxed for 6 hours. The mixture was freed from solvent, the residue was purified by column chromatography using ethyl acetate/methanol 9/1 (v/v) as eluant. 5.5 g (43.5% of theory) of a colourless amorphous substance were obtained.

Workup

  1. temperaturethe mixture was then refluxed for 6 hours
  2. customthe residue was purified by column chromatography
  3. custom5.5 g (43.5% of theory) of a colourless amorphous substance were obtained

Sources & evidence

ORD record
ord-15fb64b0243f426eb0e8ea24464000af
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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