Diisopropylethylamine → 1-(1-(4-Bromophenyl)ethyl)-4-(methylsulfonyl)piperazine

HRID 873334Notes

Reaction equation

HRID 873334 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Cl)[CH3:9])=[CH:4][CH:3]=1.[CH3:11][S:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:14])=[O:13].C(N(C(C)C)CC)(C)C>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:18]2[CH2:19][CH2:20][N:15]([S:12]([CH3:11])(=[O:14])=[O:13])[CH2:16][CH2:17]2)[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7091611-(Methylsulfonyl)piperazineHCID 145574671-Bromo-4-(1-chloroethyl)benzene

Product 1

HCID 867105341-(1-(4-Bromophenyl)ethyl)-4-(methylsulfonyl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

1-Bromo-4-(1-chloroethyl)benzene (3.46 g, 15.8 mmol), 1-methanesulfonylpiperazine (5.19 g, 31.6 mmol) and diisopropylethylamine (11.8 mL, 79 mmol) were stirred in acetonitrile (125 mL) and heated to 65° C. for 3 d. The reaction mixture was concentrated in vacuo, dissolved in EtOAc and washed with sat. NaHCO3 (aq.). The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography using silica gel and eluting with 100% isohexanes to 100% EtOAc to give the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in EtOAc
  3. washwashed with sat. NaHCO3 (aq.)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluting with 100% isohexanes to 100% EtOAc

Sources & evidence

ORD record
ord-5b5432ee24904c63a318e2973726db91
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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