N-Methylbenzylamine → N-(4-Methanesulphonamidophenacyl)-N-methyl-benzylamine

HRID 1196535Notes

Reaction equation

HRID 1196535 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:10][S:11]([NH:14][C:15]1[CH:24]=[CH:23][C:18]([C:19](=[O:22])[CH2:20]Br)=[CH:17][CH:16]=1)(=[O:13])=[O:12].C(N(CC)CC)C>C(O)C>[CH3:10][S:11]([NH:14][C:15]1[CH:24]=[CH:23][C:18]([C:19](=[O:22])[CH2:20][N:2]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH3:1])=[CH:17][CH:16]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 8471TriethylamineHCID 15592151N-(4-(2-bromoacetyl)phenyl)methanesulfonamide

Product 1

HCID 19898951N-(4-Methanesulphonamidophenacyl)-N-methyl-benzylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Methylbenzylamine (22.43 g), 4-methanesulphonamidophenacyl bromide (50 g) (see J. Med. Chem. 1966, 9, 88) and triethylamine (17 g) in ethanol (500 ml) were stirred at room temperature for 18 hours. The solvent was removed, the residue was taken up in dilute hydrochloric acid, washed with ethyl acetate and the organic layer was discarded. The aqueous layer was neutralised with sodium bicarbonate and then extracted three times with ethyl acetate. The combined organic extracts were evaporated and the residue chromatographed on silica [Merck `Kieselgel 60` (Trade Mark)] eluting with hexane containing ethyl acetate (0% up to 100%). The title compound was obtained as an oil by collection and evaporation of appropriate fractions. The oil solidified when triturated with ether, yield of the title compound 32 g.

Workup

  1. customThe solvent was removed
  2. washwashed with ethyl acetate
  3. extractionextracted three times with ethyl acetate
  4. customThe combined organic extracts were evaporated
  5. customthe residue chromatographed on silica [Merck `Kieselgel 60` (Trade Mark)]
  6. washeluting with hexane
  7. additioncontaining ethyl acetate (0% up to 100%)

Sources & evidence

ORD record
ord-26d7dcb19cb84ee9b4d049a249dd61e8
Source dataset
uspto-grants-1992_05
Patent number
US05114952

Reaction notes

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