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

HRID 2061476Notes

Reaction equation

HRID 2061476 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-25a564e08ce1411988f49158fe9c586b
Source dataset
uspto-grants-2012_10
Patent number
US08283364B2

Reaction notes

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