Bromide ion → N-[3-(4-Piperidinyl)phenyl]propanamide

HRID 1832255Notes

Reaction equation

HRID 1832255 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(I)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br-].[N-:16]=[C:17]=[O:18].[C:19](#N)[CH3:20]>>[NH:1]1[CH2:6][CH2:5][CH:4]([C:12]2[CH:13]=[C:8]([NH:16][C:17](=[O:18])[CH2:19][CH3:20])[CH:9]=[CH:10][CH:11]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 259Bromide ionHCID 6342Acetonitrile3×HCID 8082PiperidineHCID 12098Benzyl iodideHCID 105034Isocyanate

Product 1

HCID 22048836N-[3-(4-Piperidinyl)phenyl]propanamide

Reagents, catalysts & solvents 1

HCID 178435178HCID 178435178, compoundSolvent

Procedure

The library was constructed in polypropylene Robbins 46 well plates Reactor Blocks. In the initial incubation period, each well was charged with PS-TBD resin (from Argonaut Technologies, 0.280 mmol, 2.50 eq, 200 mg), and piperidine (0.120 mmol, 1.10 eq) in acetonitrile (0.500 mL) and agitated for 1 h. A solution of benzyl iodide or bromide (0.110 mmol, 1.00 eq) in acetonitrile (0.500 mL) was added to each well followed by additional acetonitrile (1.00 mL) to make a total volume of 2.00 mL and the mixture was rotated in a Robbins rotating oven at room temperature for 16 h. Then AP-Isocyanate resin (Argonaut Technologies, 250 mg, 0.430 mmol, 4.00 eq) was added to each well and reacted further at room temperature for another 12 h. The mixture was filtered and the filtrate was concentrated in vacuo to obtain the desired product that was characterized via LC-MS.

Workup

  1. customat room temperature
  2. customfor 16 h
  3. customreacted further at room temperature for another 12 h
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-082eae01d33f4417acdf0992ab481a17
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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