Diisopropylethylamine → N-(4-chloropyridin-2-yl)-1-methylpiperidine-4-carboxamide

HRID 1963723

反応式

HRID 1963723 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8](Cl)=[O:9])[CH2:4][CH2:3]1.[Cl:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:8]([CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:9])[CH:13]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 4365031-Methylpiperidine-4-carbonyl chlorideHCID 5818662-Amino-4-chloropyridine

生成物 1

HCID 69008397N-(4-chloropyridin-2-yl)-1-methylpiperidine-4-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A flask was flame dried and placed under a nitrogen atmosphere. 1-methylpiperidine-4-carbonyl chloride (1 eq) in anhydrous methylene chloride was added to the flask and brought to 0° C. To this was added the solution containing 4-chloropyridin-2-amine (1 eq), and diisopropylethylamine (5 eq) in anhydrous methylene chloride, which was stirred for 1 hour at 0° C. Reaction concentrated and partitioned between water and ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated to give the crude product. Purification on silica gel, 10% methanol in methylene chloride to yield N-(4-chloropyridin-2-yl)-1-methylpiperidine-4-carboxamide as a slightly yellow crystal solid. HPLC=2.39 min; MS: MH+=254.

後処理

  1. temperatureA flask was flame
  2. customdried
  3. custombrought to 0° C
  4. additionTo this was added the solution
  5. customReaction
  6. concentrationconcentrated
  7. custompartitioned between water and ethyl acetate
  8. customThe organic layer was separated
  9. washwashed with brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated
  12. customto give the crude product
  13. customPurification on silica gel, 10% methanol in methylene chloride

出典と根拠

ORDレコード
ord-d29a842058d24a01b12bd799e6ec409a
出典データセット
uspto-grants-2013_04
特許番号
US08415382B2

関連ノート

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