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

HRID 1409744ノート

反応式

HRID 1409744 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

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 then added in one portion under nitrogen and the resulting mixture stirred at r.t. for 17 h. The mixture is diluted with dichloroemthane (25 mL) and extracted with 3 M HCl (75 mL and 50 mL). The combined HCI layers are cooled on ice and 4 M NaOH (100 mL) is added in portions until the mixture is strongly basic (pH ˜14). The mixture is then extracted with dichloroemthane (150 mL and 100 mL) and the combined dichloromethane layers are dried over Na2SO4, filtered and concentrated to yield the title compound. LC (method 21): tR=2.57 min; Mass spectrum (APCI): m/z=253 [M+H]+.

後処理

  1. additionThe mixture is diluted with dichloroemthane (25 mL)
  2. extractionextracted with 3 M HCl (75 mL and 50 mL)
  3. temperatureThe combined HCI layers are cooled on ice and 4 M NaOH (100 mL)
  4. additionis added in portions until the mixture
  5. extractionThe mixture is then extracted with dichloroemthane (150 mL and 100 mL)
  6. dry with materialthe combined dichloromethane layers are dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-65f4f01b870f4d55893b13e90d4903aa
出典データセット
uspto-grants-2014_12
特許番号
US08921398B2

反応ノート

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