Dimethylformamide → Tert-butyl 4-(4-{2-[(6-methylpyridin-2-yl)oxy]ethyl}benzyl)piperazine-1-carboxylate

HRID 1023339Notes

Reaction equation

HRID 1023339 reaction equation
CN(C=O)C.[OH:6][CH2:7][CH2:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[CH:11][CH:10]=1.[H-].[Na+].F[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[N:33]=1>O>[CH3:38][C:34]1[N:33]=[C:32]([O:6][CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:13][N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:16][CH2:15]3)=[CH:27][CH:28]=2)[CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 960902-Fluoro-6-methylpyridineHCID 67328866Tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylate

Product 1

HCID 67327079Tert-butyl 4-(4-{2-[(6-methylpyridin-2-yl)oxy]ethyl}benzyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a DMF (10 mL) solution of tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylate (1.000 g) was added NaH (112 mg, 60% in mineral oil) at 0° C., then the resultant mixture was stirred for 1 hour. To the mixture was added 2-fluoro-6-methylpyridine (0.419 mL), then the resultant mixture was stirred at 70° C. over night. The mixture was poured into water, and extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and evaporated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=4/1 to 1/1) to afford tert-butyl 4-(4-{2-[(6-methylpyridin-2-yl)oxy]ethyl}benzyl)piperazine-1-carboxylate as a pale yellow amorphous powder (350 mg).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with water and saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=4/1 to 1/1)

Sources & evidence

ORD record
ord-8865c68e05ba4f78b6e6f40404f75f15
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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