Benzaldehyde → HCID 12082743, compound

HRID 1977903Notes

Reaction equation

HRID 1977903 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.CO>[CH2:15]([N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]1[CH2:6][C:5]1[CH:13]=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 240Benzaldehyde2×HCID 516892Sodium BicarbonateHCID 3939526HCID 3939526, compoundHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 12082743HCID 12082743, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a 100 mL round-bottomed flask equipped with N2 inlet were added 250 mg (0.984 mmol) 2-(4-bromobenzyl)-piperidine (prepared as described in Tetrahedron Letters, 7, 631 (1977)), 110 uL (1.08 mmol) benzaldehyde, 7 mL methanol, 74 mg (1.18 mmol) sodium cyanoborohydride, and a few drops of acetic acid. The reaction was stirred at room temperature, followed by additional benzaldehyde, sodium cyanoborohydride, and acetic acid, for a total of 16 hours then poured into dilute aqueous sodium bicarbonate solution, and extracted into ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using methanol/methylene chloride as eluant, and the product further purified by conversion to the hydrochloride salt in ether followed by basification using aqueous sodium hydroxide solution to afford 175 mg (52%) of an oil.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with N2 inlet
  2. extractionextracted into ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. customthe product further purified by conversion to the hydrochloride salt in ether

Sources & evidence

ORD record
ord-3d253921dbfe489a9ef41e6d9e46827d
Source dataset
uspto-grants-2001_05
Patent number
US06235750B1

Reaction notes

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