Trifluoroacetic acid → 1-[3-(2-Isopropyloxyethylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride

HRID 1975372Notes

Reaction equation

HRID 1975372 reaction equation
FC(F)(F)C(O)=O.[CH:8]([O:11][CH2:12][CH2:13][N:14]([C:22]1[CH:23]=[C:24]([CH:42]=[CH:43][CH:44]=1)[C:25]([N:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[CH2:29][CH2:28]1)=[O:26])C(OC(C)(C)C)=O)([CH3:10])[CH3:9]>ClCCl>[ClH:41].[CH:8]([O:11][CH2:12][CH2:13][NH:14][C:22]1[CH:23]=[C:24]([CH:42]=[CH:43][CH:44]=1)[C:25]([N:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 190994721-{3-[N-(2-isopropyloxyethyl)-N-tert-butoxycarbonylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine

Product 1

HCID 190994541-[3-(2-Isopropyloxyethylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

65 ml of trifluoroacetic acid are introduced into 100 ml of dichloromethane. A solution of 7.2 g of 1-{3-[N-(2-isopropyloxyethyl)-N-tert-butoxycarbonylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine is added thereto within a period of 5 minutes. After 2 hours at RT, the reaction solution is concentrated by evaporation and the residue is neutralised with sodium hydroxide solution and extracted with ether. Concentration by evaporation and treatment with ethereal hydrochloric acid yield 1-[3-(2-isopropyloxyethylamino)benzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride having a melting point of 157°-159°.

Workup

  1. waitAfter 2 hours at RT
  2. concentrationthe reaction solution is concentrated by evaporation
  3. extractionextracted with ether
  4. concentrationConcentration
  5. customby evaporation and treatment with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-8bccc7971f2244fbabec8f4d36b6f81b
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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