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

HRID 2064076Notes

Reaction equation

HRID 2064076 reaction equation
F[C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:10][CH:9]([O:8][C:6]1[CH:5]=[CH:4][C:3]([N+:12]([O-:14])=[O:13])=[C:2]([NH:15][CH:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH2:21]2)[CH:7]=1)[CH3:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 135386522-Fluoro-4-isopropoxy-1-nitrobenzene

Product 1

HCID 574239161,1-Dimethylethyl 4-({5-[(1-methylethyl)oxy]-2-nitrophenyl}amino)-1-piperidinecarboxylateYield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-fluoro-4-[(1-methylethyl)oxy]-1-nitrobenzene (D46, 276 mg, 1.39 mmol) in dimethylformamide (10 ml) was treated with 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (278 mg, 1.39 mmol) and diisopropylethylamine (0.241 ml, 1.39 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 a mixture of ethyl acetate/diethyl ether (×2). The combined extract was dried and concentrated under vacuum to afford the title compound as a yellow oil/solid (514 mg, 97%).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe residue treated with water
  3. extractionextracted with a mixture of ethyl acetate/diethyl ether (×2)
  4. extractionThe combined extract
  5. customwas dried
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6d52a82122ed402eb58d2a769754cdd8
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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