Triethylamine → 1-(2-Fluoro-4-nitrophenyl)piperidin-4-ol

HRID 56152

Reaction equation

HRID 56152 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.CCN(CC)CC.F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[F:25]>CCOC(C)=O>[F:25][C:17]1[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:16]=1[N:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 265982211-(2-Fluoro-4-nitrophenyl)piperidin-4-olYield 80.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of piperidin-4-ol (11.11 g, 0.11 mol) and Et3N (12.14 g, 0.12 mol) in EtOAc (500 mL) was added 1,2-difluoro-4-nitrobenzene (15.91 g, 0.10 mol). The mixture was stirred at rt for 24 h, and washed with water (200 mL×4). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as orange oil (19.35 g, 80%).

Workup

  1. washwashed with water (200 mL×4)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a558440d17004c44b2cb7ddab9285113
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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