Trifluoroacetic acid → 4-Methyl-5-piperazin-1-yl-benzofuran-2-carboxylic acid ethyl ester trifluoroacetic acid salt

HRID 2036047Notes

Reaction equation

HRID 2036047 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:22]=[CH:23][C:24]3[O:28][C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:26][C:25]=3[C:34]=2[CH3:35])[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:32]([O:31][C:29]([C:27]1[O:28][C:24]2[CH:23]=[CH:22][C:21]([N:18]3[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]3)=[C:34]([CH3:35])[C:25]=2[CH:26]=1)=[O:30])[CH3:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67201242Tert-butyl 4-(2-(ethoxycarbonyl)-4-methylbenzofuran-5-yl)piperazine-1-carboxylate

Product 1

HCID 671998804-Methyl-5-piperazin-1-yl-benzofuran-2-carboxylic acid ethyl ester trifluoroacetic acid saltYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 ml) was added to a stirred solution of 4-(2-Ethoxycarbonyl-4-methyl-benzofuran-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (1.4 g, 0.003 mol) in dichloromethane (10 ml) at room temperature. The reaction mixture was stirred for 2 hours. Solvent was concentrated under reduced pressure, the residue was triturated with diethyl ether (20 ml) to isolate 4-Methyl-5-piperazin-1-yl-benzofuran-2-carboxylic acid ethyl ester trifluoroacetic acid salt (1.25 g, 86.2%).

Workup

  1. concentrationSolvent was concentrated under reduced pressure
  2. customthe residue was triturated with diethyl ether (20 ml)

Sources & evidence

ORD record
ord-9dfba9e5146e4a7d93f213dae67ee0a9
Source dataset
uspto-grants-2013_11
Patent number
US08575161B2

Reaction notes

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