Potassium Carbonate → HCID 71062035, 화합물

HRID 1774316노트

반응식

HRID 1774316 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:8].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N:31]2[CH2:36][CH2:35][N:34]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[O:8])[CH2:33][CH2:32]2)=[CH:23][CH:24]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 220016181386927-90-7HCID 72545477HCID 72545477, 화합물

생성물 1

HCID 71062035HCID 71062035, 화합물수율 60%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A stirred mixture of 6-bromo-N-(2-pyridylmethyl)hexanamide (0.60 g, 2.1 mmol), 1-[2-(4-methoxyphenyl)phenyl]piperazine (0.68 g, 2.5 mmol) and K2CO3 (3.5 mmol) in acetonitrile was refluxed overnight. After cooling, the mixture was evaporated to dryness and H2O (20 mL) was added to the residue. The aqueous phase was extracted with AcOEt (2×30 mL). The collected organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was chromatographed (CHCl3/MeOH, 19:1, as eluent) to afford pure compound in 60% yield. 1H NMR (CDCl3): δ 1.35-1.42 (m, 2H), 1.53-1.63 (m, 2H), 1.68-1.78 (m, 2H), 2.28 (t, 2H, J=7.4 Hz), 2.42 (app. t, 2H), 2.65 (br s, 4H), 3.09 (br s, 4H), 3.81 (s, 3H), 4.45 (d, 2H, J=6.1 Hz), 6.12 (br t, 1H, D2O exchanged), 6.94 (d, 2H, J=8.8 Hz), 7.00 (d, 1H, J=8.0 Hz), 7.09-7.16 (m, 2H), 7.22-7.30 (m, 3H), 7.46 (d, 2H, J=8.8 Hz), 8.58 (m, 1H). GC-MS m/z 473 (M+1, 1), 472 (M+, 5), 379 (20), 282 (50), 226 (100), 210 (35).

후처리

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customthe mixture was evaporated to dryness and H2O (20 mL)
  4. additionwas added to the residue
  5. extractionThe aqueous phase was extracted with AcOEt (2×30 mL)
  6. dry with materialThe collected organic layers were dried over Na2SO4
  7. customevaporated under reduced pressure
  8. customThe crude residue was chromatographed (CHCl3/MeOH, 19:1, as eluent)
  9. customto afford pure compound in 60% yield

출처 및 근거

ORD 기록
ord-c1ab2663133049b088c8ed2233b584bc
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260400B2

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