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

HRID 661249Notes

Reaction equation

HRID 661249 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:18][NH:17][CH2:16][CH:15]([C:19]([O:21][CH3:22])=[O:20])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]([F:12])([F:11])[F:10].C(N(CC)CC)C.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=1)=[O:32]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:18][N:17]([C:31]([O:33][C:34]3[CH:35]=[CH:36][C:37]([N+:40]([O-:42])=[O:41])=[CH:38][CH:39]=3)=[O:32])[CH2:16][CH:15]([C:19]([O:21][CH3:22])=[O:20])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[CH2:8][C:9]([F:12])([F:10])[F:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58116551Methyl 5-[3-fluoro-4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate

Product 1

HCID 581165423-Methyl 1-(4-nitrophenyl) 5-[3-fluoro-4-(2,2,2-trifluoroethyl)phenyl]piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.00 g (9.52 mmol, purity 76%) of the compound from Example 76A in dichloromethane (111 ml) was admixed with 4.65 ml (3.37 g, 33.3 mmol) of triethylamine and then, at 0° C., admixed with 1.92 g (9.52 mmol) of 4-nitrophenyl chloroformate. The mixture was warmed to RT and stirred for 2 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: 5.42 g (94% of theory, purity 80%)

Workup

  1. customat 0° C.
  2. washThe reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water
  3. dry with materialthe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e911b1fc14a34cab919e3d271a63769f
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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