Reaction #312609

ord-053e612af3034dc581e0086189b8a118

Reaction equation

O=S(=O)(c1ccccc1)n1ccc2c(N3CCNCC3)cccc21
1-(phenylsulfonyl)-4-piperazin-1-yl-1H-indole
BrCc1ccccc1
benzyl bromide
CCN(CC)CC
triethyl-amine
O=S(=O)(c1ccccc1)n1ccc2c(N3CCN(Cc4ccccc4)CC3)cccc21
title product
O=S(=O)(c1ccccc1)n1ccc2c(N3CCN(Cc4ccccc4)CC3)cccc21
4-(4-Benzylpiperazin-1-yl)-1-(phenyl-sulfonyl)-1H-indole

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationconcentrated in vacuo
  2. 2
    Otherto give a residue
  3. 3
    OtherThe residue is purified by RP-HPLC

Procedure

A solution of 1-(phenylsulfonyl)-4-piperazin-1-yl-1H-indole (71 mg, 0.18 mmol) in tetrahydrofuran is treated sequentially with benzyl bromide (21 μl) and triethyl-amine (75 μl ), shaken at room temperature for 16 hr and concentrated in vacuo to give a residue. The residue is purified by RP-HPLC to give the title product, 37 mg, identfied by HPLC and mass spectral analyses (2.81 min; 432 M+H) using the LCMS conditions described in Table I.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07557098B2uspto-grants-2009_07