Piperidine → HCID 59495830, compound

HRID 219790Notes

Reaction equation

HRID 219790 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>CCO>[N+:11]([C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 59495830HCID 59495830, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Fluoro-4-nitrobenzoic acid (Combi-Blocks CA-4022, 5 g; 27.01 mmol) was dissolved in EtOH (30 mL) to which was added piperidine (8.02 mL; 81.03 mmol). The reaction mixture was stirred at RT for 24 hours, then concentrated and the residue was taken up in water (300 mL). The aqueous phase was washed with Et2O then the aqueous phase was acidified with acetic acid until pH 5. The aqueous phase was extracted with Et2O (900 mL). The combined organic phases were dried over MgSO4 and concentrated affording the title compound as an orange solid (6.18 g, 91%). 1H NMR (DMSO-d6, 300 MHz) δ 13.55 (br s, 1H), 7.89-7.86 (d, J=8.42 Hz, 1H), 7.77-7.76 (d, J=1.40 Hz, 1H), 7.60-7.57 (dd, J=8.42 Hz, 1.50 Hz, 1H), 3.23-2.98 (m, 2H), 3.21-3.05 (m, 4H), 1.63-1.58 (m, 6H). HPLC (Method A) Rt 3.88 min (Purity: 99.9%).

Workup

  1. concentrationconcentrated
  2. washThe aqueous phase was washed with Et2O
  3. extractionThe aqueous phase was extracted with Et2O (900 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-512888acb7404eb690615a8229d224d4
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

Loading…