Diisopropylethylamine → 1-(2-{4-[Bis(4-fluorophenyl)methylene]piperidin-1-yl}-2-oxoethyl)-3,3-diphenylpiperidin-2-one

HRID 1667214

반응식

HRID 1667214 반응식
[O:1]=[C:2]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:20][C:21](O)=[O:22].Cl.[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=2)=[C:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[CH:28][CH:27]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[F:45][C:42]1[CH:41]=[CH:40][C:39]([C:32]([C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=2)=[C:33]2[CH2:38][CH2:37][N:36]([C:21](=[O:22])[CH2:20][N:3]3[CH2:4][CH2:5][CH2:6][C:7]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:2]3=[O:1])[CH2:35][CH2:34]2)=[CH:44][CH:43]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 133631904-[Bis-(4-fluorophenyl)methylene]piperidine hydrochlorideHCID 673592802-(2-Oxo-3,3-diphenylpiperidin-1-yl)acetic acid

생성물 1

HCID 673589281-(2-{4-[Bis(4-fluorophenyl)methylene]piperidin-1-yl}-2-oxoethyl)-3,3-diphenylpiperidin-2-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-(2-oxo-3,3-diphenylpiperidin-1-yl)acetic acid (Example 68E) (0.144 g, 0.47 mmol) and 4-(bis(4-fluorophenyl)methylene)piperidine hydrochloride (European Journal of Medicinal Chemistry; 22, 1987; 243-250) (0.15 g, 0.47 mmol) in methylene chloride (10 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.177 g, 0.47 mmol) and diisopropylethylamine (0.4 mL). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then diluted with methylene chloride, and washed with 1 N HCl, water, 1 N NaOH, and water. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The obtained residue was purified by silica gel flash chromatography, eluting with 5% methanol/dichloromethane. 1H NMR (300 MHz, CDCl3) δ ppm 7.17-7.33 (m, 10H), 6.96-7.05 (m, 8H), 4.24 (s, 2H), 3.66 (t, J=5.5 Hz, 2H), 3.51 (t, J=6.4 Hz, 2H), 3.42-3.48 (m, 2H), 2.62-2.67 (m, 2H), 2.29-2.42 (m, 4H), 1.75-1.89 (m, 2H); MS (ESI+) m/z 577 (M+H)+.

후처리

  1. washwashed with 1 N HCl, water, 1 N NaOH, and water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe obtained residue was purified by silica gel flash chromatography
  5. washeluting with 5% methanol/dichloromethane

출처 및 근거

ORD 기록
ord-0aa0cc06f18744ccbf743362b0031d6f
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044069B2

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