Aminoethylpiperazine → 1-(2-N-Boc-aminoethyl)piperazine

HRID 260910

Reaktionsgleichung

Reaktionsgleichung von HRID 260910
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[C:10]([O:14][C:15](ON=C(C1C=CC=CC=1)C#N)=[O:16])([CH3:13])([CH3:12])[CH3:11]>O1CCOCC1.O>[C:10]([O:14][C:15]([NH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Komponenten

4

Edukt 2

HCID 8795AminoethylpiperazineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Produkt 1

HCID 15144011-(2-N-Boc-aminoethyl)piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

1-(2-aminoethyl)piperazine (1.29 g, 10 mmol) is dissolved in 20 mL of dioxane:water (1:1) mixture and 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (2.46 g, 10 mmol) is added. The mixture is then stirred until no starting material is detected on thin layer chromatography. The obtained mixture is fractionally separated by silica gel chromatography, followed by RP-HPLC to obtain 1-[2-tert-butoxycarbonylaminoethyl]piperazine. Following the procedure of Example 6, but replacing 1-benzylpiperazine with 1-[2-tert-butoxycarbonylaminoethyl]piperazine, provides the desired compound. The product of Example 3 (2.1 g, 2.03 mmol), 1-[2-tert-butoxycarbonylaminoethyl]piperazine (1.396 g, 6.09 mmol), and triethylamine (0.85 mL, 6.09 mmol) in 10 mL of methylene chloride are used. The obtained product (1.0 g) is treated with 48%-HF (4 mL) in 35 mL of acetonitrile in the procedure described in Example 5, followed by a carefully deprotection of N-tert-butoxycarbonyl group with 10% trifluoroacetic acid to obtain the pure title compound.

Aufarbeitung

  1. additionis added
  2. customThe obtained mixture is fractionally separated by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d801ae9163a74e1284e45fd1be6ad25e
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530119

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