Water → 1,1-Dimethylethyl 4-[(2-nitro-3-fluoro-5-methoxyphenyl)amino]-piperidinecarboxylate

HRID 447764Notes

Reaction equation

HRID 447764 reaction equation
[N+:1]([C:4]1[C:9](F)=[CH:8][C:7]([O:11][CH3:12])=[CH:6][C:5]=1[F:13])([O-:3])=[O:2].[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.O.C(OCC)(=O)C>CN(C)C=O.C(N(C(C)C)CC)(C)C>[N+:1]([C:4]1[C:5]([F:13])=[CH:6][C:7]([O:11][CH3:12])=[CH:8][C:9]=1[NH:14][CH:15]1[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12682914-Amino-1-Boc-piperidineHCID 100127101,3-Difluoro-5-methoxy-2-nitrobenzene

Product 1

HCID 596832591,1-Dimethylethyl 4-[(2-nitro-3-fluoro-5-methoxyphenyl)amino]-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

4-Nitro-3,5-difluoroanisole (D11) (370 mg, 2 mmol) was dissolved in dry dimethylformamide (3 ml) and diisopropylethylamine (0.4 ml), and 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (400 mg, 2 mmol) were added at room temperature. The mixture was stirred at room temperature for 18 h, then cooled to room temperature and water and ethyl acetate added. The organic layer was dried over MgSO4, filtered and evaporated, and the residue crystallised from diethyl ether to afford the title compound, 380 mg. M−−H=368.

Workup

  1. temperaturecooled to room temperature
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue crystallised from diethyl ether

Sources & evidence

ORD record
ord-2d7926662dc641918f85cc3e449e5200
Source dataset
uspto-grants-2013_07
Patent number
US08481566B2

Reaction notes

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