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

HRID 67068Notes

Reaction equation

HRID 67068 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:23](=[N-])(=[O:25])=[O:24]>N1C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[NH:22][S:23]2(=[O:25])=[O:24])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 13051020N-((2-aminophenyl)methyl)-1-benzylpiperidin-4-amineHCID 18672990Sulfurylamide

Product 1

HCID 131172113-(1-benzylpiperidin-4-yl)-3,4-dihydro-1H-2$l^{6},1,3-benzothiadiazine-2,2-dioneYield 72.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Then, 590 mg of 1-benzyl-4-[N-(o-aminobenzyl)amino]-piperidine, 600 mg of sulfurylamide and 12 ml of pyridine are mixed and refluxed with heating for 2 hours. The reaction mixture is cooled to room temperature and poured into 50 ml of ice water. The white crystals deposited are separated by filtration, washed with 10 ml of water and dried to obtain 520 mg of the desired product as crystals.

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 2 hours
  3. customThe white crystals deposited are separated by filtration
  4. washwashed with 10 ml of water
  5. customdried

Sources & evidence

ORD record
ord-e0bc648f6ef4403aaf9fa5d256bd5f38
Source dataset
uspto-grants-1982_08
Patent number
US04344945

Reaction notes

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