Hydrochloric Acid → 4-(2,3-Dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidineacetic acid

HRID 1611430ノート

反応式

HRID 1611430 の反応式
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([O:16]CC)=[O:15])[CH2:9][CH2:8]2)[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[NH:3]1.[OH-].[Na+].Cl>CO>[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9][CH2:8]2)[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[NH:3]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20750053HCID 20750053、化合物

生成物 1

HCID 220370584-(2,3-Dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidineacetic acid収率 146%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of ethyl (4-(2-keto-1-benzimidazolinyl)piperidin-1-yl)acetate (13.0 g, 42.8 mmol) in methanol (150 mL) was treated with an aqueous solution of sodium hydroxide (3 N, 30 mL, 90 mmol) and heated at reflux for 2 hours. The solution was cooled to room temperature and neutralized with the addition of concentrated hydrochloric acid (12 N, 7.5 mL). The solvent was evaporated in vacuo, and the resultant amorphous solid was dried in vacuo with heating (˜50° C.) overnight to give (4-(2-keto-1-benzimidazolinyl)piperidin-1-yl)acetic acid (17.2 g) which was used in the subsequent step without purification. MS m/z 304 (MH+); NMR(DMSO-d6): δ 1.74 (br d, 2 H), 2.53-2.67 (m, 2 H), 2.74-2.86 (m, 2 H), 3.33 (s, 2 H), 4.29-4.42 (m, 1 H), 6.97-7.05 (m, 3 H) and 7.38-7.43 (m, 1 H).

後処理

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was evaporated in vacuo
  4. customwas dried in vacuo
  5. temperaturewith heating (˜50° C.) overnight

出典と根拠

ORDレコード
ord-d5f616c088284d209d3e577b039df661
出典データセット
uspto-grants-2006_01
特許番号
US06987188B2

反応ノート

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