Potassium Carbonate → (RS) 4-[3-[2-[2-(piperidin-1-yl)ethyl]piperidin-1-yl]propoxy]-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole

HRID 1384027노트

반응식

HRID 1384027 반응식
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:14]2[N:13]=[C:12]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[N:11]([CH2:24][CH2:25][CH2:26][CH:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[N:46]1([CH2:52][CH2:53][CH:54]2[CH2:59][CH2:58][CH2:57][CH2:56][NH:55]2)[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1>CN(C)C=O>[N:46]1([CH2:52][CH2:53][CH:54]2[CH2:59][CH2:58][CH2:57][CH2:56][N:55]2[CH2:2][CH2:3][CH2:4][O:5][C:6]2[C:14]3[N:13]=[C:12]([CH2:15][O:16][C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)[N:11]([CH2:24][CH2:25][CH2:26][CH:27]4[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]4)[C:10]=3[CH:9]=[CH:8][CH:7]=2)[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2962911-(2-(Piperidin-2-yl)ethyl)piperidineHCID 211884734-(3-Bromopropoxy)-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole

생성물 1

HCID 21188663(RS) 4-[3-[2-[2-(piperidin-1-yl)ethyl]piperidin-1-yl]propoxy]-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A solution of 4-[3-bromopropoxy]-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole (77 mg, 0.124 mmol, 1 eq) in anhydrous N,N-dimethylformamide (2 ml) was treated with potassium carbonate (51.3 mg, 0.37 mmol, 2 eq) and 2-[2-(piperidin-1-yl)ethyl]piperidine (0.19 mmol, 1.5 eq). The resulting mixture was stirred at 80° C. for six hours. The reaction was quenched by the addition of water (10 ml). The aqueous fraction was extracted with ethyl acetate (3×10 ml). The organic fractions were combined, washed with water (3×10 ml), brine (1×10 ml), and then dried over sodium sulfate. The solvents were removed in vacuo to yield an oily crude product which was purified by flash chromatography to provide the title product.

후처리

  1. customThe reaction was quenched by the addition of water (10 ml)
  2. extractionThe aqueous fraction was extracted with ethyl acetate (3×10 ml)
  3. washwashed with water (3×10 ml), brine (1×10 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvents were removed in vacuo
  6. customto yield an oily crude product which
  7. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-f330498b0d224d07adb9143ecaf4dd26
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06255494B1

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