Nitrogen → {4-[3-(3,4,5-Trimethoxy-phenyl)-propionyl]-piperazin-1-yl}-acetic acid ethyl ester

HRID 1944259

반응식

HRID 1944259 반응식
N#N.CCN=C=NCCCN(C)C.Cl.CCN(CC)CC.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:34][CH2:35][C:36]([OH:38])=O)[CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31].[CH2:39]([O:41][C:42]([CH2:44][N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)=[O:43])[CH3:40]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:39]([O:41][C:42](=[O:43])[CH2:44][N:45]1[CH2:50][CH2:49][N:48]([C:36](=[O:38])[CH2:35][CH2:34][C:26]2[CH:27]=[C:28]([O:32][CH3:33])[C:29]([O:30][CH3:31])=[C:24]([O:23][CH3:22])[CH:25]=2)[CH2:47][CH2:46]1)[CH3:40]

참가 물질

8

반응물 5

HCID 947NitrogenHCID 8471TriethylamineHCID 648603,4,5-Trimethoxyhydrocinnamic acidHCID 207112Ethyl piperazine-1-acetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 59785706{4-[3-(3,4,5-Trimethoxy-phenyl)-propionyl]-piperazin-1-yl}-acetic acid ethyl ester수율 83.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

The following reaction is done in an anhydrous N2 atmosphere.) Suspend EDC HCl (376 mg, 1.96 mmol) and Et3N (275 μL, 1.96 mmol) in anhydrous DCM (2.0 mL) and stir the resulting solution for 5 min at rt. Add 3-(3,4,5-Trimethoxy-phenyl)-propionic acid (346 mg, 1.44 mmol) and DMAP (17 mg, 0.14 mmol) and stir the resulting solution for 15 min. Add 1-(Ethoxycarbonylmethyl)piperazine (43) (224 mg, 1.30 mmol) and stir the reaction solution overnight at rt. Quench reaction solution with water, separate layers and extract aqu. layer with EtOAc (3 times). Filtrate the combined organic layer through a short pad of silica gel and remove solvent. Purify the crude product by preparative radial chromatography (silica gel, EtOAc/MeOH 9+1) to obtain {4-[3-(3,4,5-Trimethoxy-phenyl)-propionyl]-piperazin-1-yl}-acetic acid ethyl ester (45) (426 mg, 83%) as a colorless oil. 1H NMR (400 MHz, CDCl3): 1.26 (t, 3H, J=7.1 Hz); 2.45-2.70 (br.m, 6H); 2.89 (t, 2H, J=7.7 Hz); 3.26 (br.s, 2H); 3.43-3.56 (br.m, 2H); 3.61-3.76 (br.m, 2H); 3.80 (s, 3H); 3.83 (s, 6H); 4.18 (q, 2H, J=7.1 Hz); 6.41 (s, 2H).

후처리

  1. customThe following reaction
  2. customQuench
  3. customreaction solution with water
  4. customseparate layers
  5. extractionextract aqu
  6. customFiltrate the combined organic layer through a short pad of silica gel and remove solvent
  7. customPurify the crude product by preparative radial chromatography (silica gel, EtOAc/MeOH 9+1)

출처 및 근거

ORD 기록
ord-945816a7e5ef4252bbabb7efdf079dc8
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394835B2

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