Succinic Acid → N-trityl piperazine, succinate salt

HRID 1772559

Reaktionsgleichung

Reaktionsgleichung von HRID 1772559
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:7](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:27]([OH:34])(=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31]>C1(C)C=CC=CC=1.CO.C1(C)C=CC=CC=1>[C:27]([OH:34])(=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31].[C:7]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 1110Succinic AcidHCID 4837PiperazineHCID 6456Trityl chloride

Produkt 1

HCID 67005131N-trityl piperazine, succinate saltAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 21867641Toluene methanolLösungsmittel

Versuchsvorschrift

To a cooled solution of piperazine (10 eq) in toluene/methanol (5:1 toluene/methanol (v:v); 5 mL/g piperazine) was added slowly a solution of trityl chloride 10 (1.0 eq) in toluene (5 mL/g trityl chloride). Upon reaction completion (1-2 hr), this solution was washed four times with water. To the resulting organic solution was added an aqueous solution of succinic acid (1.1 eq; 13 mL water/g succinic acid). This mixture was stirred for 90 min, and the solid product was collected by filtration. The crude solid was purified by two reslurries in acetone. Yield=70%.

Aufarbeitung

  1. customUpon reaction completion (1-2 hr)
  2. washthis solution was washed four times with water
  3. filtrationthe solid product was collected by filtration
  4. customThe crude solid was purified by two reslurries in acetone

Quellen und Nachweise

ORD-Eintrag
ord-09a8309ef317447ea9628f2f04f3f24c
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249243B2

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