Hydrochloric Acid → 1-Benzylpiperidine-4-acetonitrile

HRID 470626

Reaction equation

HRID 470626 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]#[N:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].Cl.[OH-].[Na+]>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]#[N:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Procedure

To a solution of benzylpiperidin-4-ylideneacetonitrile (compound of Example 26; 1 g, 4.7 mmol) in methanol (50 mL), magnesium turnings (4.58 g, 188.3 mmol) was added at 0° C. The reaction mixture was stirred at 5° C. to 10° C. for 4 h. The magnesium salts were dissolved by addition of concentrated hydrochloric acid, and the mixture was basified with 10N sodium hydroxide solution. The precipitate was filtered and extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with water (2×15 mL) followed by brine (10 mL). The organic phase obtained was dried over anhydrous sodium sulphate and evaporated to afford the title compound.

Workup

  1. filtrationThe precipitate was filtered
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. washThe combined organic layers were washed with water (2×15 mL)
  4. customThe organic phase obtained
  5. dry with materialwas dried over anhydrous sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-4aa1d79e9e7d4f9f8508f261759f8239
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Linked notes

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