Pyrrolidine → 7-Benzyloxy-2-methyl-4-pyrrolidin-1-yl-quinoline

HRID 2415461ノート

反応式

HRID 2415461 の反応式
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

3

反応物 2

HCID 31268PyrrolidineHCID 226414197-Benzyloxy-4-chloro-2-methyl-quinoline

生成物 1

HCID 226413107-Benzyloxy-2-methyl-4-pyrrolidin-1-yl-quinoline収率 75%

反応条件

温度
80 °C

実験手順

A mixture of 534 mg (1.8 mmol) of 7-benzyloxy-4-chloro-2-methyl-quinoline and 3.77 ml (45 mmol) pyrrolidine was heated at 80° C. (oil bath temperature) under an argon atmosphere for 23 h after which time the reaction was completed according to HPLC analysis. The reaction was partitioned between EtOAc and water, the aqueous layer was extracted once with EtOAc, the combined organic layers were washed with water then saturated NaCl solution, dried over magnesium sulphate and concentrated in vacuo. The residue was applied to silica gel column with CH2Cl2/MeOH/NH4OH (19:1:0.05) as eluent. Combination of the purified fractions and concentration in vacuo gave 430 mg (74.5%) of the 7-benzyloxy-2-methyl-4-pyrrolidin-1-yl-quinoline as a brown solid. ISP mass spectrum, m/e: 319.4 (M+1 calculated for C21H22N2O: 319).

後処理

  1. customThe reaction was partitioned between EtOAc and water
  2. extractionthe aqueous layer was extracted once with EtOAc
  3. washthe combined organic layers were washed with water
  4. dry with materialsaturated NaCl solution, dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. concentrationCombination of the purified fractions and concentration in vacuo

出典と根拠

ORDレコード
ord-3ab863c303974bf4a2cfcb35259e93bc
出典データセット
uspto-grants-2004_11
特許番号
US06818767B2

反応ノート

読み込み中…