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Formaldehyde → Dimethyl 4-(2,6-dichlorophenyl)-6-(2-phenylethyl)-2-(1-oxo-1-methoxy-2-propen-2-yl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 343311
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HRID 343311 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:12][C:11]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[C:10]1[C:32]([O:34][CH3:35])=[O:33].[CH3:36]N1CCNCC1.C=O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:12][C:11]([C:27](=[CH2:36])[C:28](=[O:29])[O:30][CH3:31])=[C:10]1[C:32]([O:34][CH3:35])=[O:33]
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참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 531671-MethylpiperazineHCID 70203360Dimethyl 4-(2,6-dichlorophenyl)-2-methoxycarbonylmethyl-6-(2-phenylethyl)-1,4-dihydropyridine-3,5-dicarboxylate

생성물 1

HCID 131721086Dimethyl 4-(2,6-dichlorophenyl)-6-(2-phenylethyl)-2-(1-oxo-1-methoxy-2-propen-2-yl)-1,4-dihydropyridine-3,5-dicarboxylate수율 50.9%

시약·촉매·용매 1

HCID 176
Acetic Acid
용매

실험 절차

Dimethyl 4-(2,6-dichlorophenyl)-2-methoxycarbonylmethyl-6-[2-(phenyl)ethyl]-1,4-dihydropyridine-3,5-dicarboxylate (588 mg, 1.135 m mol) and N-methylpiperazine (0.132 ml, 1.19 m mol) were dissolved in acetic acid (3 ml) and to the solution was added paraformaldehyde. The mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo and partitioned between CH2Cl2 (50 ml) and aqueous NaHCO3 solution (20 ml). The aqueous layer was extracted with CH2Cl2 (30 ml). The combined organic layer and the extract were washed with brine (10 ml), dried (MgSO4), and concentrated in vacuo to give a yellow oil. This was crystallized from ethyl acetate and isopropyl ether gave a yellow solid (270 mg, 50.9%). Second crop was obtained from the mother liquid (78 mg, 14.7%). 1H NMR (D2O) δ7.35-7.16 (m, 7H), 7-05-6.97 (m, 1H), 6.21 (br.s, 1H), 6.06 (s, 1H), 5.52 (br.s, 1H), 5.43 (br.s, 1H), 3.73 (s, 3H), 3.57 (s, 3H), 3.46 (s, 3H), 3.10-2.80 (m, 4H).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between CH2Cl2 (50 ml) and aqueous NaHCO3 solution (20 ml)
  3. extractionThe aqueous layer was extracted with CH2Cl2 (30 ml)
  4. washThe combined organic layer and the extract were washed with brine (10 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customThis was crystallized from ethyl acetate and isopropyl ether

출처 및 근거

ORD 기록
ord-f6bb277c56ab4a1a90411bd579598096
출처 데이터셋
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05861402

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