Hydrogen chloride-ethyl acetate → HCID 22393754, compound

HRID 1071634Notes

Reaction equation

HRID 1071634 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1.C(OCC)(=O)C.Cl>CO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 22393654HCID 22393654, compound

Product 1

HCID 22393754HCID 22393754, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.94 g (6.25 mmol) of tert-butyl 4-[3-(2-thienyl) propyl]-1-piperazinecarboxylate was dissolved in 20 ml of methanol, and 15 ml of a 4N hydrogen chloride-ethyl acetate solution was added. After completion of the reaction, the mixture was evaporated. The residue was adjusted to pH 11 with a 2N aqueous sodium hydroxide, then the objective product was extracted with chloroform and dried over anhydrous magnesium sulfate. The solvent was evaporated, to give 1.23 g (5.85 mmol, 93.6%) of the title compound as ayellow oil, as acrude product. 1H-NMR (400 MHz, CDCl3) δ 1.84-1.92 (m, 2H), 2.35-2.48 (m, 6H), 2.83-2.93 (m, 6H), 6.77-6.80 (m, 1H), 6.91 (dd, J 3.2 Hz, 5.2 Hz, 1H), 7.11 (dd, J=1.2 Hz, 5.2 Hz, 1H)

Workup

  1. customAfter completion of the reaction
  2. customthe mixture was evaporated
  3. extractionthe objective product was extracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e4be5686d3a84ead89ed4e5841497381
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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