Potassium Carbonate → 2-(1-(bis(4-fluorophenyl)methyl)piperidin-4-ylidene)-N-(cyclopropylmethyl)acetamide

HRID 339640

반응식

HRID 339640 반응식
Cl.[CH:2]1([CH2:5][NH:6][C:7](=[O:15])[CH:8]=[C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:4][CH2:3]1.[F:16][C:17]1[CH:31]=[CH:30][C:20]([CH:21](Cl)[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[F:16][C:17]1[CH:18]=[CH:19][C:20]([CH:21]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[N:12]2[CH2:13][CH2:14][C:9](=[CH:8][C:7]([NH:6][CH2:5][CH:2]3[CH2:4][CH2:3]3)=[O:15])[CH2:10][CH2:11]2)=[CH:30][CH:31]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27237731,1'-(Chloromethylene)bis(4-fluorobenzene)HCID 66680987N-(cyclopropylmethyl)-2-(piperidin-4-ylidene)acetamide hydrochloride

생성물 1

HCID 580653352-(1-(bis(4-fluorophenyl)methyl)piperidin-4-ylidene)-N-(cyclopropylmethyl)acetamide수율 78%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of N-(cyclopropylmethyl)-2-(piperidin-4-ylidene)acetamide hydrochloride (80.0 mg, 0.347 mmol) prepared in EXAMPLE 22e, 4,4′-difluorobenzhydryl chloride (0.105 ml, 0.555 mmol), K2CO3 (105 mg, 0.763 mmol) and KI (5.8 mg, 0.035 mmol) in acetonitrile (5 ml) was stirred under reflux for 12 hours. The reaction was quenched with H2O (20 ml), extracted with chloroform (30 ml×2), dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/hexane:30/70 to 50/50) to give 2-(1-(bis(4-fluorophenyl)methyl)piperidin-4-ylidene)-N-(cyclopropylmethyl)acetamide (107 mg, 78%) as a white solid: LCMS: 397 {M+1}+. 1H NMR (DMSO-d6)□ δ: 0.11 (m, 2H), 0.38 (m, 2H), 0.87 (m, 1H), 2.22 (m, 2H), 2.32 (m, 2H), 2.36 (m, 2H), 2.93 (m, 4H), 4.47 (s, 1H), 5.61 (s, 1H), 7.13 (m, 4H), 7.43 (m, 4H), 7.87 (t, 1H).

후처리

  1. temperatureunder reflux for 12 hours
  2. customThe reaction was quenched with H2O (20 ml)
  3. extractionextracted with chloroform (30 ml×2)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (ethyl acetate/hexane:30/70 to 50/50)

출처 및 근거

ORD 기록
ord-4e4cc702a59d468fb8dd047f8bd17543
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895551B2

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