Diisopropylethylamine → 1,1-Dimethylethyl 4-({4-chloro-5-[(1-methylethyl)oxy]-2-nitrophenyl}amino)-1-piperidinecarboxylate

HRID 2064188Notes

Reaction equation

HRID 2064188 reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:4][C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[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.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Cl:1][C:2]1[C:3]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:4][C:5]([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:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 593939321-Chloro-4-fluoro-5-nitro-2-(propan-2-yloxy)benzene

Product 1

HCID 598501521,1-Dimethylethyl 4-({4-chloro-5-[(1-methylethyl)oxy]-2-nitrophenyl}amino)-1-piperidinecarboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5-chloro-2-fluoro-4-[(1-methylethyl)oxy]-1-nitrobenzene (D83, 153 mg, 0.65 mmol) in dimethylformamide (5 ml) was treated with 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (130 mg, 0.65 mmol) and diisopropylethylamine (0.113 ml, 0.65 mmol) and stirred at approx. 80° C. for 17 hrs. The mixture was concentrated under vacuum and the residue treated with water and extracted with diethyl ether (×2). The combined extract was dried (MgSO4) and concentrated under vacuum to afford the title compound as a yellow solid (260 mg, 97%).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe residue treated with water
  3. extractionextracted with diethyl ether (×2)
  4. extractionThe combined extract
  5. dry with materialwas dried (MgSO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c53fa8aa94e74a1b82fce7e3f46bf4a2
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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