Ammonia → 4-(4-Piperidinyl)-2-pyridinamine
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[NH3:21]>[Cu-]=O>[NH:11]1[CH2:12][CH2:13][CH:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:21])[CH:7]=2)[CH2:9][CH2:10]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of tert-butyl 4-(2-chloropyridin-4-yl)piperidine-1-carboxylate (24 g, 0.08 mol, 1 equiv) in ammonia (250 mL) was added copper(I) oxide (5 g, 0.03 mols, 0.4 equiv.) and stirred 10 h at 200° C. under 2.2 MPa of ammonia. The reaction was monitored by LC-MS to completion. The mixture was cooled, extracted with dichloromethane (5×250 mL), dried over Na2SO4, then concentrated to obtain compound 4-(piperidin-4-yl)pyridin-2-amine (8.5 g, 36%).
Workup
- temperatureThe mixture was cooled
- extractionextracted with dichloromethane (5×250 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-dfce5f79c530462696a4108e98cad7ef
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09399636B2
Reaction notes
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