Ammonia → 4-(4-Piperidinyl)-2-pyridinamine

HRID 1057053Notes

Reaction equation

HRID 1057053 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]1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 57366394HCID 57366394, compound

Product 1

HCID 457887934-(4-Piperidinyl)-2-pyridinamineYield 36%

Reagents, catalysts & solvents 1

HCID 178419072HCID 178419072, compoundCatalyst

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

  1. temperatureThe mixture was cooled
  2. extractionextracted with dichloromethane (5×250 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dfce5f79c530462696a4108e98cad7ef
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

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