Triethylamine → 7-methanesulphonamido-3-(4-methanesulphonamidophenethyl)-1,2,4,5-tetrahydro-3H-3-benzazepine

HRID 329366Notes

Reaction equation

HRID 329366 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:16]=[CH:15][C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14][C:8]=2[CH:7]=1)(=[O:4])=[O:3].C([N:19]([CH2:22][CH3:23])CC)C>C(O)C>[CH3:1][S:2]([NH:5][C:6]1[CH:16]=[CH:15][C:9]2[CH2:10][CH2:11][N:12]([CH2:10][CH2:9][C:8]3[CH:14]=[CH:23][C:22]([NH:19][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[CH2:13][CH2:14][C:8]=2[CH:7]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 187651877-Methanesulphonamido-1,2,4,5-tetrahydro-3H-3-benzazepine

Product 1

HCID 198720447-methanesulphonamido-3-(4-methanesulphonamidophenethyl)-1,2,4,5-tetrahydro-3H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-Methanesulphonamido-1,2,4,5-tetrahydro-3H-3-benzazepine (0.21 g), 4-[2-(methanesulphonyloxy)ethyl]methanesulphonanilide (0.26 g) (see EP-A-0245997, Preparation 7) and triethylamine (0.12 ml) were heated at reflux temperature in ethanol for 24 hours. The solvent was removed in vacuo and the residue taken up in methylene chloride, washed with aqueous sodium bicarbonate, brine and then water. The organic layer was dried (Na2SO4), evaporated in vacuo and the residue purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 5%). The product-containing fractions were combined and evaporated to give a solid which was recrystallised to give the title compound, yield 0.05 g, m.p. 190°-193°.

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with aqueous sodium bicarbonate, brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated in vacuo
  5. customthe residue purified by column chromatography on silica eluting with methylene chloride
  6. additioncontaining methanol (0% up to 5%)
  7. customevaporated
  8. customto give a solid which
  9. customwas recrystallised

Sources & evidence

ORD record
ord-8405b31fe7af456dad00a9ef163b6ae3
Source dataset
uspto-grants-1990_01
Patent number
US04891372

Reaction notes

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