1-Methylpyrrolidine → N-(2,6-Diethyl-4-morpholin-4-yl-phenyl)-4-methyl-benzenesulfonamide

HRID 1783362Notes

Reaction equation

HRID 1783362 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([CH2:21][CH3:22])[CH:3]=1.Br[CH2:24][CH2:25][O:26][CH2:27][CH2:28]Br.C(N(CC)C(C)C)(C)C.CN1CCCC1>C(OCC)(=O)C>[CH2:8]([C:6]1[CH:7]=[C:2]([N:1]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:3]=[C:4]([CH2:21][CH3:22])[C:5]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH3:9]

Participants

6

Reactant 4

HCID 84541-MethylpyrrolidineHCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 183982Benzenesulfonamide, N-(4-amino-2,6-diethylphenyl)-4-methyl-

Product 1

HCID 67406337N-(2,6-Diethyl-4-morpholin-4-yl-phenyl)-4-methyl-benzenesulfonamideYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of N-(4-amino-2,6-diethyl-phenyl)-4-methyl-benzenesulfonamide (70 mg), bis-(2-bromoethyl)ether (33 μL), N,N-diisopropyl-ethylamine (115 μL) and N-methylpyrrolidine (0.3 mL) was heated to 180° C. for 20 minutes in a sealed microwave process vial. The mixture was diluted with ethyl acetate (20 mL), washed with brine (30 mL) and saturated aqueous potassium carbonate (30 mL), and dried over sodium sulfate. The organic phase was concentrated in vacuo to furnish 78 mg (91%) of the title compound. LC-MS (m/z) 389 (MH+); tR=2.77, (UV, ELSD) 57%, 98%. The crude product was used without further purification.

Workup

  1. washwashed with brine (30 mL) and saturated aqueous potassium carbonate (30 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-d9e8fdfc834b4946b7d476ba1a26e87f
Source dataset
uspto-grants-2009_03
Patent number
US07501414B2

Reaction notes

Loading…