Trifluoroacetic acid → 4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-1-piperidin-4-ylmethyl-piperazin-2-one

HRID 1433088Notes

Reaction equation

HRID 1433088 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][N:22]2[CH2:27][CH2:26][N:25]([S:28]([C:31]3[S:35][C:34]4[CH:36]=[C:37]([Cl:40])[CH:38]=[CH:39][C:33]=4[CH:32]=3)(=[O:30])=[O:29])[CH2:24][C:23]2=[O:41])[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[Cl:40][C:37]1[CH:38]=[CH:39][C:33]2[CH:32]=[C:31]([S:28]([N:25]3[CH2:26][CH2:27][N:22]([CH2:21][CH:18]4[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]4)[C:23](=[O:41])[CH2:24]3)(=[O:30])=[O:29])[S:35][C:34]=2[CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 690254374-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 670148114-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-1-piperidin-4-ylmethyl-piperazin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4 mL) is added to a solution of 4-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester (1.1 g, 2.0 mmol) in CH2Cl2 (15 mL). After 1 h the reaction is concentrated and the residue is dissolved in CH2Cl2 and washed with Na2CO3, dried (MgSO4) and concentrated to provide 4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-1-piperidin-4-ylmethyl-piperazin-2-one. 1H NMR (300 MHz, CDCl3) δ 7.87-7.83 (m, 3H), 7.46 (dd, 1H), 3.86 (dd, 2H), 3.45 (s, 2H), 3.23 (d, 2H), 3.07 (d, 2H), 2.54 (dt, 2H), 2.39 (s, 1H), 1.83-1.75 (m, 1H), 1.56 (d, 2H), 1.24-1.11 (m, 2H); MS (Ion spray) 428 (M+H)+.

Workup

  1. concentrationAfter 1 h the reaction is concentrated
  2. dissolutionthe residue is dissolved in CH2Cl2
  3. washwashed with Na2CO3
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9085656d67e24226b71f5d385526d1c4
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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