Dimethylformamide → HCID 86241578, compound

HRID 646871Notes

Reaction equation

HRID 646871 reaction equation
F[C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.CN(C=O)C.[N-:22]=[N+:23]=[N-:24].[Na+]>CCOC(C)=O>[N:22]([C:6]1[CH:7]=[CH:2][C:3]([N+:14]([O-:16])=[O:15])=[C:4]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=1)=[N+:23]=[N-:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 53255499HCID 53255499, compound

Product 1

HCID 86241578HCID 86241578, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(fluoro-2-nitro-phenyl)-piperidine (389 mg, 1.73 mmol, as prepared in the previous step) in 5, mL of DMF was added sodium azide (169 mg, 2.60 mmol) and the resultant mixture heated to 50° C. for 14 h, and then 80° C. for 6 h. The reaction was diluted with EtOAc (100 mL), washed with water (2×50 mL), dried (Na2SO4) and concentrated in vacuo. Purification by preparative TLC (50% EtOAc-hexane) afforded 316 mg (74%) of the title compound as a tan solid. Mass spectrum (ESI, m/z): Calcd. for C11H13N5O2, 248.1 (M+H), found 247.9.

Workup

  1. washwashed with water (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by preparative TLC (50% EtOAc-hexane)

Sources & evidence

ORD record
ord-6314ec1a423943918c18da16f94ae502
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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