Sodium Hydroxide → 6-Chloro-1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one

HRID 2064053노트

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HRID 2064053 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:16][CH2:15][N:14](C(OCC)=O)[CH2:13][CH2:12]3)[C:6]=2[CH:22]=1.[OH-].[Na+]>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[C:6]=2[CH:22]=1

참가 물질

4

반응물 2

HCID 14798Sodium Hydroxide2회HCID 13792190Ethyl 4-(6-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate

생성물 1

HCID 137921086-Chloro-1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one수율 76.2%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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온도
0 °C

실험 절차

D7 (12.0 g, 37 mmol) was suspended in a 2.5 M aqueous solution of sodium hydroxide (150 mL). The suspension was refluxed for 15 hours and then allowed to cool. The solution was acidified with 6 M HCl (˜70 mL) until no more effervescence was observed (˜pH 2) and then the pH was carefully adjusted to pH 8.5 using 2.5M aqueous NaOH whilst the solution was cooled to 0° C. The resulting precipitate was collected by filtration, washed with cold water (20 mL) and then dried under vacuum at 40° C. for 15 hours to give the title compound (7.1 g, 76% yield) as a light brown solid (Rf: Baseline (ethyl acetate)). 1H-NMR (300 MHz, DMSO-d6) □ 11.11 (1H, br s), 8.97 (1H, br s), 7.52 (1H, s), 6.99-6.97 (2H, m), 4.51-4.48 (1H, m), 3.33-3.31 (2H, m), 3.02-2.97 (2H, m), 2.48-2.46 (2H, m), 1.81-1.77 (2H, m); m.p.>300° C.

후처리

  1. temperatureThe suspension was refluxed for 15 hours
  2. temperatureto cool
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with cold water (20 mL)
  5. customdried under vacuum at 40° C. for 15 hours

출처 및 근거

ORD 기록
ord-d96671cc35674a76b1df376ce1dd926b
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288413B2

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