1-[2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-yl]-ethyl]-cyclopropanecarboxylic acid tert-butyl ester → 1-{2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-yl]-ethyl}-cyclopropanecarboxylic acid

HRID 2111761Notes

Reaction equation

HRID 2111761 reaction equation
C([O:5][C:6]([C:8]1([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[C:20]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:21]=4[S:22][CH:23]=3)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[F:30][C:28]([F:29])([F:31])[C:25]1[CH:26]=[CH:27][C:20]2[C:19]([N:16]3[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][C:8]4([C:6]([OH:7])=[O:5])[CH2:10][CH2:9]4)[CH2:14][CH2:15]3)=[CH:23][S:22][C:21]=2[CH:24]=1

Participants

3

Reactant 1

HCID 588176151-[2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-yl]-ethyl]-cyclopropanecarboxylic acid tert-butyl ester

Product 1

HCID 231124271-{2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-yl]-ethyl}-cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-{2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-yl]-ethyl}-cyclopropanecarboxylic acid tert-butyl ester, 0.7 g (1.54 mmol), was stirred in 10 mL of trifluoroacetic acid. After 2 hours the reaction mixture was concentrated to an oil. This was taken up in methanolic hydrogen chloride. The salt thus obtained was recrystallized from ethyl acetate/methanol to deliver 0.4 g (60%) of white powder as the desired carboxylic acid mp=255-7° C.

Workup

  1. concentrationAfter 2 hours the reaction mixture was concentrated to an oil
  2. customThe salt thus obtained
  3. customwas recrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-f627eb0fb1e142e2b7d7411d7227f84f
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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