N,N-bis(2-chloroethyl)-p-toluenesulphonamide → HCID 67340847, compound

HRID 1674987Notes

Reaction equation

HRID 1674987 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:15][CH2:16]Cl)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C@H:25]([NH2:27])[CH3:26])=[CH:21][CH:20]=1.CCO.O>CCN(C(C)C)C(C)C>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C@H:25]([N:27]2[CH2:16][CH2:15][N:4]([S:5]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)(=[O:7])=[O:6])[CH2:3][CH2:2]2)[CH3:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamideHCID 853000(R)-4-bromo-alpha-methylbenzylamineHCID 19096565Water ethanol

Product 1

HCID 67340847HCID 67340847, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
125 °C

Procedure

N,N-Bis(2-chloroethyl)-4-methylbenzenesulfonamide (4.0 g, 13.50 mmol) and (R)-1-(4-bromophenyl)ethanamine (2.57 g, 12.83 mmol) in DIPEA (5 mL) were stirred and heated at 125° C. for 32 hours. The resulting dark mixture was cooled to 80° C. then a mixture of EtOH/water (70/30, 20 mL) added slowly to give a brown precipitate. The precipitate was collected by filtration, washed with EtOH/water (70/30) and iso-hexane and air dried to afford (R)-1-[1-(4-bromophenyl)ethyl]-4-tosylpiperazine (4.45 g, 78%) as a brown solid, which was used without further purification.

Workup

  1. temperatureThe resulting dark mixture was cooled to 80° C.
  2. additionadded slowly
  3. customto give a brown precipitate
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with EtOH/water (70/30) and iso-hexane and air
  6. customdried

Sources & evidence

ORD record
ord-0d419342828247f0a31924524e517693
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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