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

HRID 2064165Notes

Reaction equation

HRID 2064165 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[NH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1.O.C(OCC)(=O)C>CN(C)C=O.C(N(C(C)C)CC)(C)C>[F:10][C:9]([F:12])([F:11])[C:5]1[C:6]([Cl:8])=[CH:7][C:2]([NH:16][CH:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]2)=[C:3]([N+:13]([O-:15])=[O:14])[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 6211792,4-Dichloro-5-nitrobenzotrifluorideHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 598501301,1-Dimethylethyl 4-[(4-trifluoromethyl-5-chloro-2-nitrophenyl)amino]-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
80 °C

Procedure

1,5-Dichloro-2-nitro-4-(trifluoromethyl)benzene (5.5 g) was dissolved in dry dimethylformamide (50 ml) and diisopropylethylamine (5.1 ml), and 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (5.0 g) were added at room temperature. The mixture was stirred at 80° C. for 2.5 h, then water and ethyl acetate added. The organic layer was washed with water then brine, dried over MgSO4, filtered and evaporated, and the residue was crystallised from diethyl ether to afford the subtitle compound, 6.7 g.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialbrine, dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue was crystallised from diethyl ether

Sources & evidence

ORD record
ord-b1755e0605bd4f5b85622a551fa566c6
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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