1-(2,4-Dichlorobenzyl)piperazine → 1-{2-[4-(2,4-Dichlorobenzyl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpiperidin-2-one

HRID 1667212노트

반응식

HRID 1667212 반응식
[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[O:16]=[C:17]1[C:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:21][CH2:20][CH2:19][N:18]1[CH2:35][C:36](O)=[O:37].Cl.C(N=C=NCCCN(C)C)C>ClC(Cl)C>[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[CH2:4][N:5]1[CH2:6][CH2:7][N:8]([C:36](=[O:37])[CH2:35][N:18]2[CH2:19][CH2:20][CH2:21][C:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]2=[O:16])[CH2:9][CH2:10]1

참가 물질

5

반응물 3

HCID 4111791-(2,4-Dichlorobenzyl)piperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673592802-(2-Oxo-3,3-diphenylpiperidin-1-yl)acetic acid

생성물 1

HCID 452748211-{2-[4-(2,4-Dichlorobenzyl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpiperidin-2-one

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

반응 조건

온도
85 °C

실험 절차

A solution of 1-(2,4-dichlorobenzyl)piperazine (0.415 g, 1.693 mmol), 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (0.498 g, 1.608 mmol; Example 68E) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.389 g, 2.031 mmol) were stirred together in dichloroethane (0.5 mL) at room temperature for 2 hours. The reaction was then heated to 85° C. and stirred overnight. The reaction was cooled, loaded onto a SF25-40 column (Analogix®) and the product eluted using a gradient of 5% ethyl acetate/hexanes to 100% ethyl acetate over 30 minutes, then holding at 100% ethyl acetate for 15 minutes (Flow=45 mL/minute) to yield the title compound. 1H NMR (300 MHz, CDCl3) δ 7.42-7.36 (m, 2H), 7.32 (s, 11H), 4.23 (s, 2H), 3.65 (s, 2H), 3.57 (s, 2H), 3.49 (dd, J=6.5, 13.6, 4H), 2.72-2.56 (m, 2H), 2.48 (s, 4H), 1.94-1.74 (m, 2H); MS (ESI+) m/z 536.1 (M+H)+.

후처리

  1. temperatureThe reaction was cooled
  2. washthe product eluted
  3. customover 30 minutes
  4. waitholding at 100% ethyl acetate for 15 minutes

출처 및 근거

ORD 기록
ord-016caec976e54ffb9f78f65524927b63
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044069B2

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