Sodium Carbonate → HCID 22596144, 화합물

HRID 2301944노트

반응식

HRID 2301944 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH2:16])[CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38])(OCC)=O>O.C(#N)C>[C:29]1(=[O:38])[N:16]([CH:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:12][CH2:13][CH2:14][CH3:15])[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]12

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 22596141HCID 22596141, 화합물

생성물 1

HCID 22596144HCID 22596144, 화합물수율 38%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of 1-(3′,4′-dimethoxyphenyl)pentylamine (0.3 grams, 1.34 mmol) and sodium carbonate (0.15 grams, 1.45 mmol) in a mixture of water (10 milliliters) and acetonitrile (10 milliliters) was added N-carbethoxyphthalimide (0.29 grams, 1.34 mmol). The resulting solution was stirred for 3 hours at room temperature, the acetonitrile was evaporated and a two phase mixture resulted. The organic phase was extracted into methylene chloride, dried over magnesium sulfate and concentrated to afford 0.41 grams of crude product as an oil. The crude product was purified by flash chromatography (silica gel, 30% ethyl acetate/hexane) to afford 0.18 grams (38%) of the product as an oil: 1H NMR (CDCl3) δ7.88-7.63(m, 4H), 7.20-7.07(m, 2H),6.82-6.76(m, 1H), 5.34-5.18(m, 1H), 3.89(s, 3H), 3.85(s, 3H),2.66-2.43(m, 1H),2.40-2.17(m, 1H), 1.50-1.20(m, 2H), 0.96-0.81(m, 3H). 13C NMR (CDCl3) δ1.68.5, 148.8, 148.5, 133.8, 132.5, 131.9, 123.1, 120.6, 111.6, 110.8, 55.9, 55.8, 55.0, 30.9, 29.2, 22.3, 13.9.

후처리

  1. customthe acetonitrile was evaporated
  2. customa two phase mixture resulted
  3. extractionThe organic phase was extracted into methylene chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto afford 0.41 grams of crude product as an oil
  7. customThe crude product was purified by flash chromatography (silica gel, 30% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-613fecbff44e4eb59e07857a64bbe779
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06429221B1

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