Diisopropylethylamine → 4'-[1-Oxo-2-(N-benzyl-N-((1,2,3,4-tetrahydro-2-naphthyl)-methyl)amino)ethyl]methanesulfonanilide

HRID 1029749Notes

Reaction equation

HRID 1029749 reaction equation
[CH2:1]([NH:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Br[CH2:30][C:31]([C:33]1[CH:43]=[CH:42][C:36]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])=[CH:35][CH:34]=1)=[O:32]>CC(C)=O>[O:32]=[C:31]([C:33]1[CH:43]=[CH:42][C:36]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])=[CH:35][CH:34]=1)[CH2:30][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15592151N-(4-(2-bromoacetyl)phenyl)methanesulfonamideHCID 197742682-Benzylaminomethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 197742564'-[1-Oxo-2-(N-benzyl-N-((1,2,3,4-tetrahydro-2-naphthyl)-methyl)amino)ethyl]methanesulfonanilide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Benzylaminomethyl-1,2,3,4-tetrahydronaphthalene (XXXIV) (2.8 g), N,N-diisopropyl-N-ethylamine (1.44 g) and 4'-(2-bromoacetyl)methanesulfonanilide (Temple, D. L. et al., J. Med. Chem., 19(5), 626-633 (1976)) (3.27 g) were dissolved in acetone (40 ml) and stirred 18 hours at ambient temperature. The solvent was evaporated and the residue was dissolved in CH2Cl2, which was washed with H2O, dried (MgSO4) and evaporated. The HCl salt was made by dissolving the residue in MeOH/concentrated HCl, concentrating, and triturating the residue with 2-PrOH and ether. The solid product, 4'-[1-oxo-2-(N-benzyl-N-((1,2,3,4-tetrahydro-2-naphthyl)methyl)-amino)ethyl]methanesulfonanilide.HCl (XXXIII.HCl), 3 g, had NMR and mass spectra consistent with the structure indicated. It was used without further purification.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwhich was washed with H2O
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. dissolutionby dissolving the residue in MeOH/concentrated HCl
  7. concentrationconcentrating
  8. customtriturating the residue with 2-PrOH and ether
  9. customIt was used without further purification

Sources & evidence

ORD record
ord-c98ab576a9494466820e24792c0d3766
Source dataset
uspto-grants-1992_04
Patent number
US05102914

Reaction notes

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