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

HRID 1904175

反応式

HRID 1904175 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-483dd1139f19449084535fe7a6099335
出典データセット
uspto-grants-1989_06
特許番号
US04837003

関連ノート

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