1-Methylpiperazine → HCID 12945852, compound

HRID 325957Notes

Reaction equation

HRID 325957 reaction equation
CN1CCNCC1.C1(S(NCCC2C=CC(CC(Cl)=O)=CC=2)(=O)=O)C=CC=CC=1.Cl.[CH3:31][N:32]1[CH2:37][CH2:36][N:35]([C:38](=[O:58])[CH2:39][C:40]2[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][NH:48][S:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)(=[O:51])=[O:50])=[CH:42][CH:41]=2)[CH2:34][CH2:33]1>N1C=CC=CC=1>[CH3:31][N:32]1[CH2:33][CH2:34][N:35]([C:38](=[O:58])[CH2:39][C:40]2[CH:41]=[CH:42][C:43]([CH2:46][CH2:47][NH:48][S:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)(=[O:51])=[O:50])=[CH:44][CH:45]=2)[CH2:36][CH2:37]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 12945882HCID 12945882, compoundHCID 131713489HCID 131713489, compound

Product 1

HCID 12945852HCID 12945852, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To an ice-cooled solution of 3.0 g. (30 mmol) N-methylpiperazine and 100 ml. anhydrous pyridine are added portionwise, with stirring, in the course of one hour, 10.1 g. (30 mmol) 4-(2-benzenesulphonamidoethyl)-phenylacetyl chloride. Subsequently, the reaction mixture is allowed to warm up to 20° C., then heated for 5 hours at 90° C., cooled and poured into about 500 ml. ice water. The mixture is extracted with methylene chloride and the methylene chloride phase, after drying with anhydrous sodium sulphate, is evaporated. The residue is taken up in diethyl ether and the hydrochloride precipitated with ethereal hydrochloric acid. After recrystallization from ethanol, there are obtained 8.7 g. (66% of theory) 4-(2-benzenesulphonamidoethyl)-phenylacetic acid [4-methylpiperazide]hydrochloride; m.p. 168° C.

Workup

  1. temperatureheated for 5 hours at 90° C.
  2. temperaturecooled
  3. additionpoured into about 500 ml
  4. extractionThe mixture is extracted with methylene chloride
  5. dry with materialthe methylene chloride phase, after drying with anhydrous sodium sulphate
  6. customis evaporated
  7. customthe hydrochloride precipitated with ethereal hydrochloric acid
  8. customAfter recrystallization from ethanol, there
  9. customare obtained 8.7 g

Sources & evidence

ORD record
ord-dd4fcd0bd49f4510a8f38de02f9a5e52
Source dataset
uspto-grants-1984_04
Patent number
US04443477

Reaction notes

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