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

HRID 260910

반응식

HRID 260910 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d801ae9163a74e1284e45fd1be6ad25e
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05530119

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