Tetrahydrofuran → HCID 22990123, compound

HRID 1169442Notes

Reaction equation

HRID 1169442 reaction equation
[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:12][CH:11]=2)C=CC=CC=1.C1COCC1.C([Li])CCC.[CH3:45][C:46]1[CH:61]=[CH:60][C:49]([CH2:50][O:51][C:52]2[CH:53]=[C:54]([CH:57]=[CH:58][CH:59]=2)[CH:55]=O)=[CH:48][CH:47]=1>CCCCCC.O>[CH3:45][C:46]1[CH:61]=[CH:60][C:49]([CH2:50][O:51][C:52]2[CH:53]=[C:54]([CH:57]=[CH:58][CH:59]=2)/[CH:55]=[CH:9]/[C:10]2[CH:11]=[CH:12][C:13]([CH2:16][N:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)=[CH:14][CH:15]=2)=[CH:48][CH:47]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 6933133-[(4-methylbenzyl)oxy]benzaldehydeHCID 22990018HCID 22990018, compoundHCID 178418339Butyllithium

Product 1

HCID 22990123HCID 22990123, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

To a mixture comprising triphenyl[4-(piperidinomethyl)benzyl]phosphonium bromide (1.06 g) and THF (10 ml) was added dropwise under a nitrogen atmosphere a 1.6 M solution of butyllithium in hexane (1.28 ml), and the resulting mixture was stirred for 30 minutes. To this reaction mixture was added 3-(4-methylbenzyloxy)benzaldehyde (453 mg), and the resulting mixture was stirred at room temperature for one hour, was then mixed with water (100 ml) and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride, was dried with anhydrous sodium sulfate and was then evaporated under reduced pressure to remove the solvent. The resulting residue was subjected to purification using column chromatography (ethyl acetate/triethylamine=20/1) and to recrystallization to obtain (E)-1-[4-[3-(4-methylbenzyloxy)styryl]benzyl]piperidine (compound 97) (330 mg) as colorless crystals.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for one hour
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialwas dried with anhydrous sodium sulfate
  5. customwas then evaporated under reduced pressure
  6. customto remove the solvent
  7. customThe resulting residue was subjected to purification
  8. customto recrystallization

Sources & evidence

ORD record
ord-c9cfaa836db548cea2adff96604c4e1c
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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