Benzaldehyde → 1-Benzylpiperidine

HRID 1614987Notes

Reaction equation

HRID 1614987 reaction equation
Br[C:2]1CCON=1.[CH2:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH3:8].C(=O)[C:15]1[CH:20]=[CH:19]C=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[CH2:7]([N:9]1[CH2:12][CH2:13][CH2:2][CH2:11][CH2:10]1)[C:8]1[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 219834983-Bromo-4,5-dihydroisoxazole

Product 1

HCID 761901-Benzylpiperidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Bromo-4,5-dihydroisoxazole III-14 is dissolved in methylene chloride (0.06 M with respect to isxozaole) after which triethylamine (2.5 equiv) and benzaldehyde (1.25 equiv) are added followed by sodium triacetoxyborohydride (1.5 equiv). The reaction is allowed to stir for 16 h after which point is diluted with ethyl acetate and washed with dilute NaOH and then brine. The organic layer is then dried over sodium sulfate and concentrated under vacuum to provide crude material which was purified using flash silica gel chromatography (ethyl acetate/hexanes) to provide N-benzylpiperidine III-19 as a white solid. [M−H]−=308.1 m/z. Activity: A.

Workup

  1. additionare added
  2. washwashed with dilute NaOH
  3. dry with materialThe organic layer is then dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto provide crude material which
  6. customwas purified

Sources & evidence

ORD record
ord-2bcccd54cbc04bb4aa2546c86cdcc146
Source dataset
uspto-grants-2014_07
Patent number
US08765735B2

Reaction notes

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