Piperidine → 2-(Piperidin-1-yl)benzaldehyde

HRID 1824480Notes

Reaction equation

HRID 1824480 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C=O)C>[N:16]1([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 20621572-(Piperidin-1-yl)benzaldehydeYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of o-fluorobenzaldehyde (1.24 gm, 10 mmol), potassium carbonate (2.76 gm, 20 mmol), and piperidine (1.7 gm, 20 mmol) was refluxed in dry DMF for 6 hrs. After the completion of reaction DMF was distilled out at vaccum and 5 ml of water was added to the residue and extracted the product with ethyl acetate (10 ml×2). Organic layer was dried over sodium sulphate and evaporated the solvent to afford 1.8 gm of product (8) (90.5%) 1HNMR CDCl3 (Spectrum 9): 1.68(m, 6H), 3.05(m, 4H), 7.05(m, 2H), 7.45(dd, 1H), 7.75(dd, 1H).

Workup

  1. distillationwas distilled out at vaccum and 5 ml of water
  2. additionwas added to the residue
  3. extractionextracted the product with ethyl acetate (10 ml×2)
  4. dry with materialOrganic layer was dried over sodium sulphate
  5. customevaporated the solvent

Sources & evidence

ORD record
ord-528f4103d1a04abd80e280783f2ad730
Source dataset
uspto-grants-2006_05
Patent number
US07041830B2

Reaction notes

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