Dimethylformamide → Tert-butyl 4-({1-[2-(4-cyanophenyl)ethyl]-4-hydroxypiperidin-4-ylmethyl}amino)benzoate

HRID 967781Notes

Reaction equation

HRID 967781 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:18][CH2:17][C:14]3([CH2:16][O:15]3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2].[C:19](=[O:22])([O-])[O-:20].[K+].[K+].C[N:26]([CH3:29])C=O>O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:18][CH2:17][C:14]([CH2:16][NH:26][C:29]3[CH:7]=[CH:8][C:3]([C:19]([O:20][C:14]([CH3:17])([CH3:16])[CH3:13])=[O:22])=[CH:4][CH:5]=3)([OH:15])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 858197211-[2-(4-Cyanophenyl)ethyl]piperidin-4-spiro-2'-oxirane

Product 1

HCID 69732795Tert-butyl 4-({1-[2-(4-cyanophenyl)ethyl]-4-hydroxypiperidin-4-ylmethyl}amino)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound (0.48 g) obtained in Step 3 of Example 1, the compound (0.44 g) obtained in Step 1, potassium carbonate (0.55 g) and anhydrous dimethylformamide (5 mL) was stirred at 95 to 105° C. for three hours under nitrogen atmosphere. Water (30 mL) was added to the resulting mixture and the residue was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The residue (1.1 g) obtained by removal of the solvent was purified by silica gel column chromatography (Chromatorex NH™)(eluent; hexane:ethyl acetate=1:1 to ethyl acetate) to obtain the titled compound (0.55 g) as crystals.

Workup

  1. extractionthe residue was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-94f5966afdd84210bbaeea4fdddeb8f0
Source dataset
uspto-grants-2005_10
Patent number
US06956046B2

Reaction notes

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