Diethyl Ether → HCID 10337918, compound

HRID 1196911Notes

Reaction equation

HRID 1196911 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.CCOCC.[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH:29]=[O:30])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH:29]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[OH:30])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 100136024-Piperidineacetaldehyde, 1-(phenylmethyl)-HCID 178418676HCID 178418676, compound

Product 1

HCID 10337918HCID 10337918, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of a solution of 4-fluorophenyl-magnesium bromide in ether (2 M, 12.5 mL, 25 mmol) and anhydrous tetrahydrofuran (25 mL) was stirred at ambient temperature under a nitrogen atmosphere. A solution of 1-benzyl-4-formylmethylpiperidine (3.6 g, 16.6 mmol) in anhydrous tetrahydrofuran (25 mL) was added dropwise. The reaction mixture was stirred for 19 hours, then it was poured onto a saturated ammonium chloride solution, mixed and extracted three times with ethyl acetate (50 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. Column chromatography (ethyl acetate:hexanes:1:1) gave the product, a pale yellow solid (Rf =0.08, 2.7 g):mp=84°-86° C.; 1H-NMR:7.4-7.25(m,7H), 7.0(t,2H,J=8), 4.7(dd,1H,J=8,6), 3.45(s,2H), 2.9-2.75(m,2H), 2.1-1.2(m,10H); HR-MS:Calcd for C20H24FNO:313.1842; Found:313.1862.

Workup

  1. stirringThe reaction mixture was stirred for 19 hours
  2. additionmixed
  3. extractionextracted three times with ethyl acetate (50 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customColumn chromatography (ethyl acetate:hexanes:1:1) gave the product

Sources & evidence

ORD record
ord-faeccee90c324f1cb3cc297708be5283
Source dataset
uspto-grants-1992_05
Patent number
US05116846

Reaction notes

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