Water → HCID 59850148, compound

HRID 2064120Notes

Reaction equation

HRID 2064120 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[F:12].C(N(C(C)C)CC)(C)C.[NH2:22][CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1.O>CN(C)C=O>[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:22][CH:23]2[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 157514831-Chloro-2,5-difluoro-4-nitrobenzene

Product 1

HCID 59850148HCID 59850148, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1-Chloro-2,5-difluoro-4-nitrobenzene (D1) (1.18 mmol, 228 mg) was dissolved in dry dimethylformamide (2 ml) and diisopropylethylamine (1 eq., 1.18 mmol, 0.209 ml), 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (1 eq., 1.18 mmol, 236 mg) were added at room temperature and the mixture was stirred at 50° C. overnight. The crude mixture was then cooled to room temperature and water (150 ml) was added; the aqueous solution was extracted with ethyl acetate (2×); organics were alternatively washed with brine and water (2×). The organics were combined dried over Na2SO4, filtered and the solvent was evaporated to afford the title compound, 340 mg, 80%, bright orange solid, M+−H=372.

Workup

  1. extractionthe aqueous solution was extracted with ethyl acetate (2×)
  2. washorganics were alternatively washed with brine and water (2×)
  3. dry with materialThe organics were combined dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ca7c927711fa40988347d847bb340a01
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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