N-Ethylbenzylamine → N-Benzyl-N-ethyl-4-methanesulphonamidophenethylamine

HRID 345038Notes

Reaction equation

HRID 345038 reaction equation
S(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=1)(=O)(=O)C.[CH2:19]([NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:20]>C(O)C>[CH2:22]([N:21]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=1)[CH2:19][CH3:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 84352N-EthylbenzylamineHCID 149859624-Methanesulphonamidophenethyl mesylate

Product 1

HCID 19813439N-Benzyl-N-ethyl-4-methanesulphonamidophenethylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methanesulphonamidophenethyl mesylate (10 g, 34 mmole) and N-ethylbenzylamine (10 ml, 67 mmole) were heated at reflux temperature in ethanol (80 ml) for 3 hours. The solvent was evaporated, the residue taken up in 2M hydrochloric acid and washed twice with methylene chloride. The aqueous layer was basified with sodium bicarbonate (to pH ~12) and extracted with methylene chloride. The latter organic extract was dried (MgSO4) and evaporated to give an oil which solidified when triturated with diisopropyl ether. The solid was filtered off and discarded and the filtrate was evaporated in vacuo to give the title compound as an oil, yield 4.4 g.

Workup

  1. customThe solvent was evaporated
  2. washwashed twice with methylene chloride
  3. extractionextracted with methylene chloride
  4. extractionThe latter organic extract
  5. dry with materialwas dried (MgSO4)
  6. customevaporated
  7. customto give an oil which
  8. customtriturated with diisopropyl ether
  9. filtrationThe solid was filtered off
  10. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-5c4f4c380bcd45009b0bb31ca061f0e8
Source dataset
uspto-grants-1991_10
Patent number
US05055473

Reaction notes

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