Triethylamine → Tert-butyl 4-hydroxy-4-{[(3-nitroquinolin-4-yl)amino]methyl}piperidine-1-carboxylate

HRID 1469236ノート

反応式

HRID 1469236 の反応式
[NH2:1][CH2:2][C:3]1([OH:16])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[CH:27][C:26]=1[N+:35]([O-:37])=[O:36]>ClCCl>[OH:16][C:3]1([CH2:2][NH:1][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]=[CH:27][C:26]=2[N+:35]([O-:37])=[O:36])[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:7][CH2:8]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 112758084-Chloro-3-nitroquinolineHCID 23396319tert-Butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 57515384Tert-butyl 4-hydroxy-4-{[(3-nitroquinolin-4-yl)amino]methyl}piperidine-1-carboxylate収率 82.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate (78.4 mmol, prepared as described above) in dichloromethane (300 mL) was added triethylamine (11 mL, 79 mmol) and 4-chloro-3-nitroquinoline (12.7 g, 61.2 mmol). The mixture was stirred at rt for 1 h, then heated at reflux for 1 h. The solution was transferred to a separatory funnel and extracted with water (100 mL). The organic layer was isolated and upon standing a precipitate formed. The solid was isolated by filtration and washed with dichloromethane and water and dried. Additional solid precipitated from the mother liquor and was isolated. The two yellow solids were combined and dried to yield tert-butyl 4-hydroxy-4-{[(3-nitroquinolin-4-yl)amino]methyl}piperidine-1-carboxylate (20.23 g, 82%).

後処理

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. customThe solution was transferred to a separatory funnel
  4. extractionextracted with water (100 mL)
  5. customThe organic layer was isolated
  6. customformed
  7. customThe solid was isolated by filtration
  8. washwashed with dichloromethane and water
  9. customdried
  10. customAdditional solid precipitated from the mother liquor
  11. customwas isolated
  12. customdried

出典と根拠

ORDレコード
ord-061653483f3542999667c343e5e669c7
出典データセット
uspto-grants-2015_04
特許番号
US09006264B2

反応ノート

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