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

HRID 2064053ノート

反応式

HRID 2064053 の反応式
[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

参加物

4

反応物 2

HCID 14798Sodium Hydroxide2 回HCID 13792190Ethyl 4-(6-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d96671cc35674a76b1df376ce1dd926b
出典データセット
uspto-grants-2012_10
特許番号
US08288413B2

反応ノート

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