4-(Piperidin-1-yl)aniline → HCID 22124623, compound

HRID 1857964Notes

Reaction equation

HRID 1857964 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][N:3]=1.[N:15]1([C:21]2[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C([N-]C(C)C)(C)C.[Li+]>C1COCC1.C(O)(=O)C>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][N:3]=[C:2]([NH:25][C:24]3[CH:23]=[CH:22][C:21]([N:15]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)=[CH:27][CH:26]=3)[CH:11]=2)[CH:6]=[CH:7][C:8]1=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 4135014-(Piperidin-1-yl)anilineHCID 2724682Lithium diisopropylamideHCID 22124621HCID 22124621, compound

Product 1

HCID 22124623HCID 22124623, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of (XV, where R2 is ethyl) (100 mg, 0.52 mmol), 4-(1-piperidinyl)aniline (0.26 g, 1.12 mmol) in THF (5.0 mL) under nitrogen at -78° C. was treated with a solution (0.8 mL, 1.2 mmol) of lithium diisopropylamide (1.5 M in cyclohexane), then the temperature was allowed to rise slowly to 20° C. overnight. The resulting solution was treated with 3 drops of glacial acetic acid and concentrated to a dark residue that was purified that purified by silica gel chromatography eluting with EtOAc. The product fractions were pooled and concentrated to a foam that was crystallized to give ethyl-7-(4-(piperidin-1-yl)phenylamino)-1H -[1,6]naphthyridin-2-one (79 mg, 44%): mp (CH2Cl2 /hexanes) 137-139° C.

Workup

  1. concentrationconcentrated to a dark residue that
  2. customwas purified
  3. customthat purified by silica gel chromatography
  4. washeluting with EtOAc
  5. concentrationconcentrated to a foam that
  6. customwas crystallized

Sources & evidence

ORD record
ord-d7590e087a90407f855354fa20f6c771
Source dataset
uspto-grants-2000_11
Patent number
US06150359

Reaction notes

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