4-(4-Oxopiperidin-1-yl)benzonitrile → 4-(4-Benzyl-4-hydroxy-1-piperidinyl)benzonitrile

HRID 731542Notes

Reaction equation

HRID 731542 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:10]=[C:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1>C1COCC1>[CH2:1]([C:11]1([OH:10])[CH2:12][CH2:13][N:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 110198874-(4-Oxopiperidin-1-yl)benzonitrileHCID 178418336HCID 178418336, compound

Product 1

HCID 591866274-(4-Benzyl-4-hydroxy-1-piperidinyl)benzonitrileYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzylmagnesium chloride (1.90 mL of a 2M solution in THF, 3.80 mmol) at −78° C. was treated with 4-(4-oxo-1-piperidinyl)benzonitrile (prepared according to the procedure described in Synthesis 1981, 606-608, 0.30 g, 1.51 mmol), and was allowed to warm to room temperature overnight. The reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl and the aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were dried (MgSO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography eluting with 20% ethyl acetate in hexanes to give the desired product (0.087 g, 20%). MS (ESI) m/e 293 (M+H)+.

Workup

  1. customprepared
  2. customdescribed in Synthesis 1981, 606-608, 0.30 g, 1.51 mmol), and
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel chromatography
  9. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f94c99daf5174f6d981442e7e7b2de7b
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Reaction notes

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