Diethyl Ether → 1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinecarbaldehyde

HRID 423608Notes

Reaction equation

HRID 423608 reaction equation
[CH3:1][CH:2]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[CH2:11][CH2:10]2)[O:6][N:5]=1)[CH3:3].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[CH3:3][CH:2]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([CH:15]=[O:16])[CH2:11][CH2:10]2)[O:6][N:5]=1)[CH3:1]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 57930076{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 866387441-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinecarbaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol (prepared as in Example 20, Step 3, 1.50 g, 6.33 mmol) in CH2Cl2 (30 mL) was treated with pyridinium chlorochromate (2.09 g, 9.49 mmol). The reaction mixture was stirred at ambient temperature for 5 h. Et2O (50 mL) was added, and the mixture was stirred for 10 min, filtered through a plug of Celite® on top of a layer of silica gel and the filtrate was concentrated. The resulting brown residue was mixed with Et2O (100 mL) and filtered. The filtrate was dried over Na2SO4, filtered and concentrated to give 1.10 g (78%) of 1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinecarbaldehyde as a light brown oil which was used without further purification. 1H NMR (400 MHz, CDCl3): δ 9.69 (s, 1H), 4.15-4.00 (m, 2H), 3.30-3.20 (m, 2H), 2.88 (septet, 1H, J=7.0 Hz), 2.55-2.45 (m, 1H), 2.10-1.95 (m, 2H), 1.80-1.65 (m, 2H), 1.27 (d, 6H, J=6.9 Hz).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. filtrationfiltered through a plug of Celite® on top of a layer of silica gel
  3. concentrationthe filtrate was concentrated
  4. additionThe resulting brown residue was mixed with Et2O (100 mL)
  5. filtrationfiltered
  6. dry with materialThe filtrate was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5df0996591e54128ba5d5e1701181586
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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