Potassium Carbonate → 4-(6-Methoxy-3-nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1890439Notes

Reaction equation

HRID 1890439 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([O:25][CH3:26])[N:17]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.CN(C=O)C>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([NH:1][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([O:25][CH3:26])[N:17]=2)[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 27950292-Chloro-6-methoxy-3-nitropyridine

Product 1

HCID 671308354-(6-Methoxy-3-nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-amino-1-Boc-piperidine (commercial; 6.7 g, 35 mmol), 2-chloro-6-methoxy-3-nitro-pyridine (1 eq.) and K2CO3 (1 eq.) in MeCN (100 mL) and DMF (30 mL) was heated at 60° C. for 3 h. The mixture was filtered and concentrated in vacuo. The residue was taken up in ether/water 1:1, the org. phase dried over MgSO4 and concentrated. The residue was triturated with EA and filtered to afford 4.5 g of pure product. The filtrate was concentrated and purified by CC (Hept/EA 9:1, 4:1, 2:1) to give another 4 g of product. In total 8.5 g (70% yield) of a yellow solid were obtained.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dry with materialphase dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was triturated with EA
  6. filtrationfiltered

Sources & evidence

ORD record
ord-d46bb63cb7c34534852b299b8e0f1466
Source dataset
uspto-grants-2013_08
Patent number
US08507478B2

Reaction notes

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