Triethylamine → HCID 11211291, compound

HRID 1696816Notes

Reaction equation

HRID 1696816 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[C:13]([CH:15]3[CH2:20][NH:19][CH2:18][CH2:17][N:16]3[CH3:21])[O:12][N:11]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[F:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1.[OH-].[Na+]>ClCCl>[F:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([N:19]2[CH2:18][CH2:17][N:16]([CH3:21])[CH:15]([C:13]3[O:12][N:11]=[C:10]([C:7]4[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=4)[N:14]=3)[CH2:20]2)=[O:35])=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 678794-Fluorobenzoyl chlorideHCID 66618243HCID 66618243, compound

Product 1

HCID 11211291HCID 11211291, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-[3-(4-fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-1-methyl-piperazine dihydrochloride (0.285 g, 0.86 mmol) in anhydrous dichloromethane (6 mL), under nitrogen atmosphere, triethylamine (374 mL, 2.7 mmol) and 4-fluorobenzoyl chloride (102 mL, 0.86 mmol) were subsequently added at 0° C. The reaction mixture was allowed to warm at room temperature and stirred for 2 h. NaOH 1N (6 mL) was added and the phases were separated. The organic layer was washed sequentially with NaOH 1N (6 mL) and with water, then was dried over sodium sulphate and evaporated under reduced pressure. Purification of the crude by flash chromatography (silica gel, eluent: DCM/MeOH/NH4OH 99/1/0.1) afforded (4-fluoro-phenyl)-{3-[3-(4-fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-4-methyl-piperazin-1-yl}-methanone (0.12 g).

Workup

  1. customthe phases were separated
  2. washThe organic layer was washed sequentially with NaOH 1N (6 mL) and with water
  3. dry with materialwas dried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customPurification of the crude by flash chromatography (silica gel, eluent: DCM/MeOH/NH4OH 99/1/0.1)

Sources & evidence

ORD record
ord-95fb1b118f364b1caf3580efd22b3f4f
Source dataset
uspto-grants-2012_04
Patent number
US08163775B2

Reaction notes

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