Acetic Acid → 1-(5-chloropyrimidin-2-yl)-N-cyclopropylpiperidin-4-amine

HRID 68794ノート

反応式

HRID 68794 の反応式
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH:15]1([NH2:18])[CH2:17][CH2:16]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([NH:18][CH:15]3[CH2:17][CH2:16]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 682896071-(5-Chloropyrimidin-2-yl)piperidin-4-one

生成物 1

HCID 682895731-(5-chloropyrimidin-2-yl)-N-cyclopropylpiperidin-4-amine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

1-(5-Chloropyrimidin-2-yl)piperidin-4-one (1.5 g) is dissolved in anhydrous dichloromethane (25 mL) and cyclopropylamine (0.42 g) is added followed by glacial acetic acid (0.80 mL). Sodium triacetoxyborohydride (1.8 g) is added in one portion under nitrogen atmosphere and the resulting mixture is stirred at room temperature for 17 h. The mixture is diluted with dichloromethane (25 mL) and extracted with 3 M aqueous HCl (75 mL and 50 mL). The combined HCl layers are cooled on ice and 4 M aqueous NaOH solution (100 mL) is added in portions until the mixture is strongly basic (pH˜14). The mixture is extracted with dichloromethane (150 mL and 100 mL) and the combined organic layers are dried over Na2SO4, filtered and concentrated to yield the title compound.

後処理

  1. extractionextracted with 3 M aqueous HCl (75 mL and 50 mL)
  2. temperatureThe combined HCl layers are cooled on ice and 4 M aqueous NaOH solution (100 mL)
  3. additionis added in portions until the mixture
  4. extractionThe mixture is extracted with dichloromethane (150 mL and 100 mL)
  5. dry with materialthe combined organic layers are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-28cc83bc354d43b49d93ff6c3724d679
出典データセット
uspto-grants-2014_09
特許番号
US08822471B2

反応ノート

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