Triethylamine → 3-Methyl 1-(4-nitrophenyl) 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-1,3-dicarboxylate

HRID 661233Notes

Reaction equation

HRID 661233 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][NH:14][CH2:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:31]>ClCCl>[F:21][C:2]([F:1])([F:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][N:14]([C:30]([O:32][C:33]3[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=3)=[O:31])[CH2:13][CH:12]([C:16]([O:18][CH3:19])=[O:17])[CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58116537Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate

Product 1

HCID 581164903-Methyl 1-(4-nitrophenyl) 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.62 g (19.8 mmol, purity 90%) of the compound from Example 53A in dichloromethane (211 ml) was admixed with 9.65 ml (7.00 g, 69.2 mmol) of triethylamine and then admixed at 0° C. with 3.99 g (19.8 mmol) of 4-nitrophenyl chloroformate. The mixture was warmed to RT and stirred for 1 h. The reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 10.3 g (91% of theory, purity 81%)

Workup

  1. washThe reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water
  2. dry with materialthe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f7e67ae17467456c9b37d03d87ed0a3d
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

Loading…