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Sodium Iodide → 1-(3-(12H-dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-4-piperidinecarboxylic acid ethyl ester

HRID 1416332
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HRID 1416332 반응식
Br[CH2:2][CH2:3][CH:4]=[C:5]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9][O:8][C:7]2[CH:17]=[CH:18][CH:19]=[CH:20][C:6]1=2.[CH2:21]([O:23][C:24]([CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])[CH3:22].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[CH2:21]([O:23][C:24]([CH:26]1[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH:4]=[C:5]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][CH2:9][O:8][C:7]3[CH:17]=[CH:18][CH:19]=[CH:20][C:6]2=3)[CH2:28][CH2:27]1)=[O:25])[CH3:22]
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참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 17127115-(3-Bromopropylidene)benzo[d][1,3]benzodioxocine

생성물 1

HCID 508523541-(3-(12H-dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-4-piperidinecarboxylic acid ethyl ester수율 47%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
65 °C

실험 절차

A mixture of 12-(3-bromo-1-propylidene)-12H-dibenzo[d,g][1,3]dioxocin (4.0 g, 12 mmol, prepared as described in example 1), 4-piperidinecarboxylic acid ethyl ester (1.9 g, 12 mmol), anhydrous potassium carbonate (5.0 g) and sodium iodide (0.2 g) in N,N-dimethylformamide (40 ml) was heated at 60-70° C. for 5 h. After cooling, the inorganic salts were filtered off and washed with benzene (40 ml), and the filtrate was diluted with additional benzene (120 ml). The benzene solution was washed with water (3×50 ml), dried over MgSO4 and evaporated in vacuo. The oily residue (4.8 g) was purified by chromatography on silica gel using a mixture of benzene and ethyl acetate as eluent to give 1-(3-(12H-dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-4-piperidinecarboxylic acid ethyl ester as an oil (2.3 g, 47%).

후처리

  1. temperatureAfter cooling
  2. filtrationthe inorganic salts were filtered off
  3. washwashed with benzene (40 ml)
  4. additionthe filtrate was diluted with additional benzene (120 ml)
  5. washThe benzene solution was washed with water (3×50 ml)
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe oily residue (4.8 g) was purified by chromatography on silica gel using
  9. additiona mixture of benzene and ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-45ebe3a78eb24dd291e4cb0b0df644f3
출처 데이터셋
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05912262

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