Triethylamine → 4-Nitrophenyl 4,4-difluoropiperidin-1-carboxylate

HRID 1514379Notes

Reaction equation

HRID 1514379 reaction equation
Cl.[F:2][C:3]1([F:9])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:19]>ClCCl.C(OCC)(=O)C>[F:2][C:3]1([F:9])[CH2:8][CH2:7][N:6]([C:18]([O:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[O:19])[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 27583514,4-Difluoropiperidine hydrochloride

Product 1

HCID 576576134-Nitrophenyl 4,4-difluoropiperidin-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4,4-difluoropiperidin hydrochloride (2.15 g, 14 mmol) in 30 mL of dichloromethane was added triethylamine (5.7 ml, 41 mmol), followed by 4-nitrophenyl chloroformate 40 (3.0 g, 15 mmol). After 1 h, the reaction was diluted with ethyl acetate and was washed with 3×30 mL of sat. NaHCO3, and 1×30 mL brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford 4-nitrophenyl 4,4-difluoropiperidin-1-carboxylate 41 (3.9 g, 100% yield). 1H-NMR (400 MHz, CDCl3): δ 8.26 (m, 2H), 7.30 (m, 2H), 3.76 (m, 4H), 2.09 (m, 4H). MS 286.1 (calc'd) 287.1 (M+H, found).

Workup

  1. washwas washed with 3×30 mL of sat. NaHCO3, and 1×30 mL brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7bae7f3d3c4b4eb8a2f2443502da7d4f
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

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