Triethylamine → 3-Ethyl 1-(4-nitrophenyl) 5-(4-ethylphenyl)piperidine-1,3-dicarboxylate

HRID 661205Notes

Reaction equation

HRID 661205 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH2:14]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][NH:26][CH2:25][CH:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:23]2)=[CH:18][CH:17]=1)[CH3:15].C(N(CC)CC)C>ClCCl>[CH2:14]([C:16]1[CH:17]=[CH:18][C:19]([CH:22]2[CH2:27][N:26]([C:2]([O:4][C:5]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)=[O:3])[CH2:25][CH:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:23]2)=[CH:20][CH:21]=1)[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58002384Ethyl 5-(4-ethylphenyl)piperidine-3-carboxylate

Product 1

HCID 580024743-Ethyl 1-(4-nitrophenyl) 5-(4-ethylphenyl)piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 1.93 g (9.57 mmol) of 4-nitrophenyl chloroformate were added slowly to 2.5 g (9.57 mmol) of ethyl 5-(4-ethylphenyl)piperidine-3-carboxylate, the compound from Example 17A, and 1.94 g (19.1 mmol) of triethylamine in 292 ml of dichloromethane. The mixture was stirred at RT for 2 h. For workup, the reaction mixture was washed first with saturated aqueous sodium hydrogencarbonate solution, then with water. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by means of preparative HPLC. Yield: 2.66 g (64% of theory)

Workup

  1. washFor workup, the reaction mixture was washed first with saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-1bb3df3b477948bfb39eafe2502dce43
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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