Triethylamine → 1-(3,4-Difluorobenzoyl)-3-(RS)-(4-phenylpiperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine

HRID 380469노트

반응식

HRID 380469 반응식
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH:14]3[CH:18]([C:19]4[CH:23]=[CH:22][S:21][CH:20]=4)[CH2:17][NH:16][CH2:15]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[F:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[F:41])[C:35](Cl)=[O:36]>C(Cl)Cl>[F:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[F:41])[C:35]([N:16]1[CH2:17][CH:18]([C:19]2[CH:23]=[CH:22][S:21][CH:20]=2)[CH:14]([CH2:13][N:10]2[CH2:9][CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12][CH2:11]2)[CH2:15]1)=[O:36]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27245193,4-Difluorobenzoyl chlorideHCID 206944833-(SR)-(4-phenyl piperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine

생성물 1

HCID 183648201-(3,4-Difluorobenzoyl)-3-(RS)-(4-phenylpiperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine수율 78.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 0.023 g (0.071 mmol) of 3-(SR)-(4-phenylpiperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine and 0.079 mL of Et3N in 2 mL of CH2Cl2 was added 0.059 g (0.28 mmol) of 3,4-difluorobenzoyl chloride and the reaction mixture was stilled for 0.5 h. The reaction mixture was partitioned between CH2Cl2 and sat'd NaHCO3 solution. The organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chomatography (silica, acetone: hexanes, 1:3) to give 0.026 g of the title compound. 1H NMR (CDCl3) δ7.17-7.49 (m, 9H), 7.13 and 7.08 (s, 1H), 7.04 and 6.99 (d, 1H, J=4.6 Hz),4.08-4.15 (m, 2H); Mass Spectrum (CI) m/e=482 (M+1).

후처리

  1. customThe reaction mixture was partitioned between CH2Cl2 and sat'd NaHCO3 solution
  2. dry with materialThe organic fraction was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chomatography (silica, acetone: hexanes, 1:3)

출처 및 근거

ORD 기록
ord-79c3f57b767a4452be5485cb6aa68644
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303593B1

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