Triethylamine → (4-Bromo-2,6-dimethyl-phenyl)-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 1692372

반응식

HRID 1692372 반응식
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6]([OH:8])=O)=[C:4]([CH3:12])[CH:3]=1.C(Cl)(=O)C(Cl)=O.CCN(CC)CC.[N:26]1([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:30][CH2:29][CH2:28][CH2:27]1>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([C:6]([N:34]2[CH2:35][CH2:36][CH:31]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:32][CH2:33]2)=[O:8])=[C:9]([CH3:11])[CH:10]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 787034-(1-Pyrrolidinyl)piperidineHCID 119590064-bromo-2,6-dimethylbenzoic acid

생성물 1

HCID 66901599(4-Bromo-2,6-dimethyl-phenyl)-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone수율 76.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

A suspension of 0.344 g (1.5 mmol) 4-bromo-2,6-dimethyl-benzoic acid [Fuson, R. C.; Scott, S. L.; Lindsey, R. V., Jr. Journal of the American Chemical Society (1941), 63, 1679-82] in 5 ml of CH2Cl2 was treated at RT with two drops of DMF; then, a solution of 0.14 ml=0.21 g (1.6 mmol) of oxalyl chloride in 3 ml of CH2Cl2 was added drop by drop below 25° C. and the reaction mixture was stirred of 1 hour. After removal of the solvents by evaporation in a high vacuum, the residue was dissolved again in 10 ml of CH2Cl2 and the solution cooled down to 0° C.; then, 0.42 ml=0.30 g (3.0 mmol) of Et3N was added while stirring, followed by 0.23 g (1.5 mmol) of 4-pyrrolidin-1-yl-piperidine. The reaction mixture was subsequently warmed up to RT. After 60 hours, it was poured into crashed ice and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 95:5) to give 0.42 g (76%) of the title compound as light yellow oil. MS: 365.0 (MH+, 1 Br).

후처리

  1. customAfter removal of the solvents
  2. customby evaporation in a high vacuum
  3. dissolutionthe residue was dissolved again in 10 ml of CH2Cl2
  4. stirringwhile stirring
  5. temperatureThe reaction mixture was subsequently warmed up to RT
  6. waitAfter 60 hours
  7. additionit was poured
  8. extractionextracted twice with CH2Cl2
  9. washthe organic phases were washed with water
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 95:5)

출처 및 근거

ORD 기록
ord-28c52ab0bd084c458d52b1e4c9439e46
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153805B2

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