Chlorine → HCID 57916261, compound

HRID 1881689Notes

Reaction equation

HRID 1881689 reaction equation
[OH:1][C:2]1([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[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.[NH2-:21].[Na+].ClCl>C1C=CC=CC=1>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:2]2([O:1][CH2:12][CH2:11][CH2:13][N:21]3[CH2:4][CH2:3][CH2:2][CH2:7]3)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[CH:16]=1

Participants

5

Reactant 3

HCID 24526ChlorineHCID 24533Sodium amideHCID 57916274HCID 57916274, compound

Product 1

HCID 57916261HCID 57916261, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 4-hydroxy-4-(pyridin-3-yl)piperidine-1-carboxylate (2 g) was dissolved in benzene (20 ml), sodium amide (10 eq.) was added at 25° C. and the mixture was stirred at this temperature for 15 min. The corresponding chlorine compound (1.2 eq.) was then added and the mixture was heated under reflux for 16 h. When the reaction had ended (TLC control), the mixture was cooled to 0° C. and hydrolysis was carried out with ice. The aqueous phase was extracted with ethyl acetate. The organic phase was then washed successively with water and saturated NaCl solution and dried over Na2SO4. The solvent was removed on a rotary evaporator and the crude product obtained was purified by column chromatography (silica gel, MC/methanol, 95:5).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 h
  3. customhydrolysis
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washThe organic phase was then washed successively with water and saturated NaCl solution
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-1e4ad13bdda9425faa317378b7a6dc03
Source dataset
uspto-grants-2012_11
Patent number
US08318769B2

Reaction notes

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