Diisopropylethylamine → 2-Fluoro-N-(1-methyl-4-piperidinyl)-4-nitrobenzamide

HRID 2234378Notes

Reaction equation

HRID 2234378 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)=[O:6]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3026792-Fluoro-4-nitrobenzoic acidHCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 580097692-Fluoro-N-(1-methyl-4-piperidinyl)-4-nitrobenzamideYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-4-nitrobenzoic acid (Aldrich; 3 g, 16.21 mmol), 4-Amino-1-methylpiperidine (Fluorochem; 2.03 g, 17.83 mmol), HATU (6.77 g, 17.83 mmol), DIPEA (8.5 mL, 48.63 mmol) and DMF (30 mL) were combined and stirred at ambient temperature for 18 hrs. Solvents evaporated and partitioned between DCM (200 ml) and water (100 ml). The aqueous phase was re-extracted with DCM (100 ml). The combined organic phases were dried (MgSO4) and evaporated. The resultant material was taken up in DCM and purified on silica eluting with a gradient of 0-5% 2M ammonia in MeOH/DCM then 5% 2M ammonia in MeOH/DCM. Fractions containing product were combined and evaporated to give the title compound as a yellow solid (2.67 g, 59%)

Workup

  1. customSolvents evaporated
  2. custompartitioned between DCM (200 ml) and water (100 ml)
  3. extractionThe aqueous phase was re-extracted with DCM (100 ml)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. customevaporated
  6. custompurified on silica eluting with a gradient of 0-5% 2M ammonia in MeOH/DCM
  7. additionFractions containing product
  8. customevaporated

Sources & evidence

ORD record
ord-a4ecb489d4a1426eb37782a8decd4505
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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