Ethanamine, 2-fluoro-, hydrochloride → N-(2-chloroethyl)-(3-benzyl-5,6-diethylpyrazine-2-yl oxy) acetamide

HRID 330070

Reaction equation

HRID 330070 reaction equation
[C:1](Cl)(=[O:6])[C:2](C)(C)C.C(O[O:12][C:13]1[C:18]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:17][C:16]([CH2:26][CH3:27])=[C:15]([CH2:28][CH3:29])[N:14]=1)(=O)C.[ClH:30].F[CH2:32][CH2:33][NH2:34].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(N(CC)CC)C.C(Cl)(Cl)Cl>[Cl:30][CH2:32][CH2:33][NH:34][C:1](=[O:6])[CH2:2][O:12][C:13]1[C:18]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:17][C:16]([CH2:26][CH3:27])=[C:15]([CH2:28][CH3:29])[N:14]=1

Participants

8

Reactant 4

HCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 11430Potassium CarbonateHCID 62493Pivaloyl chlorideHCID 86743689(3-Benzyl-5,6-diethylpyrazine-2-yl oxy) acetate

Product 1

HCID 15170451N-(2-chloroethyl)-(3-benzyl-5,6-diethylpyrazine-2-yl oxy) acetamideYield 88.8%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent2×

Procedure

Pivaloyl chloride (3.66 g, 30 mM) was added dropwise at -5° C. to compound 655 (8.62 g, 28.7 mM) and triethylamine (4.2 ml, 30 mM) dissolved in tetrahydrofuran (50 ml), then the mixture was stirred for 30 minutes. Chloroform (30 ml) in solution with 2-fluoroethylamine hydrochloride (3.48 g) and triethylamine (4.2 ml) was added dropwise thereto with cooling at 0° to -5° C. then the mixture was stirred for 1 hour with ice cooling and 4 hours at room temperature. Dilute aqueous potassium carbonate was added to the reaction mixture and the mixture was extracted three times with chloroform. The extract was dried with anhydrous magnesium sulfate, and concentrated in vacuo. The residue was charged on a column of silica gel (C-200, 175 g) and eluted successively with benzene and benzene-ethyl acetate (5:1) to obtain the product. (9.21 g, yield: 88.8%).

Workup

  1. temperaturewith cooling at 0° to -5° C.
  2. stirringthe mixture was stirred for 1 hour with ice cooling and 4 hours at room temperature
  3. extractionthe mixture was extracted three times with chloroform
  4. dry with materialThe extract was dried with anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe residue was charged on a column of silica gel (C-200, 175 g)
  7. washeluted successively with benzene and benzene-ethyl acetate (5:1)
  8. customto obtain the product

Sources & evidence

ORD record
ord-fd7256a37c514635bd620f41b69d38a7
Source dataset
uspto-grants-1990_01
Patent number
US04894453

Linked notes

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