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

HRID 1469236Notes

Reaction equation

HRID 1469236 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-061653483f3542999667c343e5e669c7
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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