Water → (R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate

HRID 931286Notes

Reaction equation

HRID 931286 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3]1.C(N(CC)CC)C.Cl[C:21]1[N:26]=[C:25]([NH2:27])[C:24]([N+:28]([O-:30])=[O:29])=[CH:23][CH:22]=1.O>C(#N)C>[NH2:27][C:25]1[N:26]=[C:21]([N:2]2[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3]2)[CH:22]=[CH:23][C:24]=1[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 44828658Ethyl (3R)-piperidine-3-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 131735158(R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylateYield 86.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)-ethyl piperidine-3-carboxylate hydrochloride salt (1.2 g, 6.21 mmol) in acetonitrile (20 mL) was added triethylamine (2.61 mL, 18.64 mmol). The mixture was stirred for 10 min at room temperature. 6-Chloro-3-nitropyridin-2-amine (753 mg, 4.31 mmol) was added and the reaction mixture was stirred at 80° C. for 3 h. The mixture was cooled to room temperature and water was added. The mixture was extracted with ethyl acetate. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford (R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate (1.1 g). MS (ES+APCI) (M+H) 295.2.

Workup

  1. stirringthe reaction mixture was stirred at 80° C. for 3 h
  2. temperatureThe mixture was cooled to room temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e9b6fb66f384ac4bceba6c7f527ff8c
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

Loading…