Ammonium Chloride → HCID 88888621, compound

HRID 2202812Notes

Reaction equation

HRID 2202812 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].[Cl-].[NH4+]>C(OCC)C>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C:24]([OH:27])([C:9]2[C:10]([Cl:13])=[CH:11][CH:12]=[C:7]([Cl:6])[N:8]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 276852,5-DichloropyridineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 88888621HCID 88888621, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyl lithium (1.7M, 1 mL) was added dropwise to a solution of 2,5-dichloro-pyridine (2.0 g, 13.57 mmol) in diethyl ether (20 mL), under nitrogen at −78° C. and stirred for 1 hour. 4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (2.69 g, 13.57 mmol) in diethyl ether (5 mL) was added dropwise at −78° C. and the reaction mixture stirred for 0.5 hours before warming to room temperature. A solution of saturated aqueous ammonium chloride was added and the mixture extracted into ethyl acetate. The organics washed with brine, dried over sodium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 5-20% ethyl acetate/cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (1.44 g).

Workup

  1. stirringthe reaction mixture stirred for 0.5 hours
  2. extractionthe mixture extracted into ethyl acetate
  3. washThe organics washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed by evaporation under vacuum
  7. customThe residue was purified by flash chromatography on silica eluting with 5-20% ethyl acetate/cyclohexane
  8. additionThe fractions containing the desired product
  9. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-9f1645f2d9dd47d7a3e6d9bba89a75df
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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