N,N-bis(2-chloroethyl)-p-toluenesulphonamide → 1-[1-(4-Bromo-phenyl)-1-methyl-ethyl]-4-(toluene-4-sulfonyl)-piperazine

HRID 717075Notes

Reaction equation

HRID 717075 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.Cl[CH2:13][CH2:14][N:15]([CH2:26][CH2:27]Cl)[S:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>C(N(C(C)C)CC)(C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:11]2[CH2:27][CH2:26][N:15]([S:16]([C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)(=[O:18])=[O:17])[CH2:14][CH2:13]2)([CH3:9])[CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamideHCID 230091162-(4-Bromophenyl)propan-2-amine

Product 1

HCID 898128531-[1-(4-Bromo-phenyl)-1-methyl-ethyl]-4-(toluene-4-sulfonyl)-piperazine

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 1-(4-bromo-phenyl)-1-methyl-ethylamine (400 mg, 1.84 mmol) in diisopropylethylamine (4 mL) was added N,N-bis(2-chloroethyl)-4-methylbenzene sulphonamide (500 mg, 1.68 mmol) and the reaction subjected to microwave irradiation at 150° C. for 9 h afterwhich time the reaction was concentrated in vacuo and the crude residue purified by reverse phase preparative HPLC-MS to afford 1-[1-(4-bromo-phenyl)-1-methyl-ethyl]-4-(toluene-4-sulfonyl)-piperazine as a peach solid (375 mg, 47%).

Workup

  1. customirradiation at 150° C. for 9 h afterwhich time the reaction
  2. concentrationwas concentrated in vacuo
  3. customthe crude residue purified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-a588321891274149b21604d5864d63c0
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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