4-[(2-Fluorophenoxy)methyl]piperidine → 2-Tert-butoxy 6-[2-[4-(2-fluorophenoxymethyl)piperidino]ethyl]pyrazine

HRID 606218Notes

Reaction equation

HRID 606218 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]([CH:12]=[CH2:13])[N:7]=1)([CH3:4])([CH3:3])[CH3:2].[F:14][C:15]1[CH:28]=[CH:27][CH:26]=[CH:25][C:16]=1[O:17][CH2:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(O)C>[C:1]([O:5][C:6]1[CH:11]=[N:10][CH:9]=[C:8]([CH2:12][CH2:13][N:22]2[CH2:21][CH2:20][CH:19]([CH2:18][O:17][C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[F:14])[CH2:24][CH2:23]2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 171780514-[(2-Fluorophenoxy)methyl]piperidineHCID 222482762-Tert-butoxy-6-vinylpyrazine

Product 1

HCID 222480162-Tert-butoxy 6-[2-[4-(2-fluorophenoxymethyl)piperidino]ethyl]pyrazineYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After dissolving 262 mg of 2-tert-butoxy-6-vinylpyrazine and 401 mg of 4-(2-fluorophenoxymethyl)piperidine [CAS No. 63608-34-4] in 3 ml of ethanol, the mixture was stirred for 2 days at 80° C. The reaction solution was concentrated under reduced pressure, and the residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (67 mg, 12% yield).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-12155ac42927403abe0e8c2a5f3aa0d6
Source dataset
uspto-grants-2011_03
Patent number
US07915274B2

Reaction notes

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