Triethylamine → (6-Cyanohexyl)bis(2-phthalimidoethyl)amine

HRID 1904175

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HRID 1904175 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[N:9].[C:10]1(=[O:36])[N:14]([CH2:15][CH2:16][NH:17][CH2:18][CH2:19][N:20]2[C:24](=[O:25])[C:23]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]3[C:21]2=[O:30])[C:13](=[O:31])[C:12]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:11]12.C(N(CC)CC)C>CN(C=O)C>[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:17]([CH2:16][CH2:15][N:14]1[C:13](=[O:31])[C:12]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:11]2[C:10]1=[O:36])[CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30])#[N:9]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 88737Heptanenitrile, 7-bromo-HCID 3547072,2'-[iminobis(ethane-2,1-diyl)]bis(1H-isoindole-1,3(2H)-dione)

생성물 1

HCID 19811078(6-Cyanohexyl)bis(2-phthalimidoethyl)amine수율 41%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A mixture of 6-bromohexylcyanide (13.88g, 0.073 mol), bis(2-phthalimidoethyl)amine (26.52g, 0.073 mol), and triethylamine (7.37g, 0.073 mol) in DMF (120 ml) was heated at 100° C. for 20 hours. After cooling, the precipitate which had formed was removed by filtration and the filtrate was poured into ice (1000 ml). The aqueous solution was extracted with dichloromethane (3×200 ml). The combined organic extracts were washed with brine and dried over Na2SO4. Removal of the solvent under reduced pressure gave crude product which was chromatographed on silica gel (hexanes - 30% ethyl acetate/hexanes gradient elution). Impure fractions were rechromatographed to provide a total of 14.1g of (6-cyanohexyl)bis(2-phthalimidoethyl)amine (41%) as an oil. The produce was one spot on tlc. The ir spectrum was consistent with the assigned structure.

후처리

  1. temperatureAfter cooling
  2. customthe precipitate which had formed
  3. customwas removed by filtration
  4. additionthe filtrate was poured into ice (1000 ml)
  5. extractionThe aqueous solution was extracted with dichloromethane (3×200 ml)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. customRemoval of the solvent under reduced pressure
  9. customgave crude product which
  10. customwas chromatographed on silica gel (hexanes - 30% ethyl acetate/hexanes gradient elution)
  11. customImpure fractions were rechromatographed

출처 및 근거

ORD 기록
ord-483dd1139f19449084535fe7a6099335
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04837003

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