Ammonium Chloride → HCID 57366393, compound

HRID 1897934Notes

Reaction equation

HRID 1897934 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C([Li])CCC.[O:14]=[C:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[Cl:1][C:2]1[N:3]=[C:4]([CH2:8][C:15]2([OH:14])[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:19][CH2:20]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 876016-Chloro-2-picolineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 57366393HCID 57366393, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.22 ml of 2-chloro-6-methylpyridine in 12.5 ml of tetrahydrofuran was added 1.4 ml of a hexane solution containing 1.58 M n-butyl lithium at 0° C., followed by stirring the reaction mixture at 0° C. for 30 minutes. After cooling down to −78° C., a solution of 403.7 mg of tert-butyl 4-oxo-1-piperidinecarboxylate in 1 ml of tetrahydrofuran was added to the solution, followed by gradually warming up the reaction mixture to −40° C. To the reaction mixture was added saturated aqueous ammonium chloride solution, followed by extracting with chloroform. The resulting chloroform layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1−3/2) to give the title compound as a pale yellow oil.

Workup

  1. temperatureAfter cooling down to −78° C.
  2. temperatureby gradually warming up the reaction mixture to −40° C
  3. extractionby extracting with chloroform
  4. washThe resulting chloroform layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1−3/2)

Sources & evidence

ORD record
ord-5f96f27ad196430d8e69687c7a28321f
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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