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

HRID 876260Notes

Reaction equation

HRID 876260 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].C(N(CC)CC)C.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)=[O:28]>ClCCl>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][N:13]([C:27]([O:29][C:30]3[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=3)=[O:28])[CH2:12][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)=[CH:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58002552Methyl 5-(4-ethylphenyl)piperidine-3-carboxylate

Product 1

HCID 580023823-Methyl 1-(4-nitrophenyl) 5-(4-ethylphenyl)piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

10.0 g (40.4 mmol) of the compound from Example 2A were initially charged in 135 ml of dichloromethane and cooled to 0° C., and 11.2 ml (8.2 g, 80.9 mmol) of triethylamine and 8.5 g (40.4 mmol) of 4-nitrophenyl chloroformate were added. The reaction mixture was allowed to warm to room temperature over a period of 2 h. For work-up, the mixture was twice washed with water, and the organic phase was dried over sodium sulphate. The solvent was removed under reduced pressure and the residue was dried under high vacuum. Yield: 16.5 g (83% of theory)

Workup

  1. temperatureto warm to room temperature over a period of 2 h
  2. washFor work-up, the mixture was twice washed with water
  3. dry with materialthe organic phase was dried over sodium sulphate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-ba9f81bdab7b4713bc97c6141fd0f975
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

Loading…