Water → 1,1-Dimethylethyl 4-[(5-methoxy-4-chloro-2-nitrophenyl)amino]-piperidinecarboxylate

HRID 2064152Notes

Reaction equation

HRID 2064152 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](F)=[CH:4][C:3]=1[O:12][CH3:13].[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>[CH3:13][O:12][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[C:5]([NH:14][CH:15]2[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]2)[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12682914-Amino-1-Boc-piperidineHCID 598501961-Chloro-4-fluoro-2-methoxy-5-nitrobenzene

Product 1

HCID 598501431,1-Dimethylethyl 4-[(5-methoxy-4-chloro-2-nitrophenyl)amino]-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

2-Chloro-4-nitro-5-fluoroanisole (D42) (300 mg) was dissolved in dry dimethylformamide (3 ml) and diisopropylethylamine (0.3 ml), and 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (330 mg) were added at room temperature. The mixture was stirred for 3 h, then water and ethyl acetate added. The organic layer was dried over MgSO4, filtered and evaporated, and the residue was crystallised from diethyl ether to afford the title compound, 400 mg.

Workup

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

Sources & evidence

ORD record
ord-8c1e4dff41b747eba27e6bc4dfa2a307
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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