Dimethylformamide → HCID 18353389, compound

HRID 429869Notes

Reaction equation

HRID 429869 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[CH2:4][CH2:3]1.BrCCC(N)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C([N:31]([CH2:34][CH3:35])CC)C.[CH3:36]N(C=O)C>C(OCC)(=O)C>[C:24]([O:23][C:21]([NH:31][CH2:34][CH2:35][CH2:36][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[CH2:4][CH2:3]1)=[O:22])([CH3:25])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 14193053HCID 14193053, compoundHCID 18326618HCID 18326618, compound

Product 1

HCID 18353389HCID 18353389, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-(piperidin-4-yl)-4-fluorobenzonitrile hydrochloride (2.5 g, 10.4 mmol), 3-bromo-1-tert-butoxycarbonylpropylamine (3.22 g, 13.5 mmol) and triethylamine (3.76 ml, 27 mmol) in DMF (12 ml) was stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and washed with saturated bicarbonate solution, water×2 and brine. Drying and solvent evaporation gave after flash chromatography (silica gel, ethyl acetate) 3.1 g of 2-[1-(3-tert-butoxycarbonylaminopropyl)piperidin-4-yl]-4-fluorobenzonitrile. This material was dissolved in EtOAc (200 mL), cooled to 0° C. and HCl gas was bubbled into the solution for 15 minutes. The reaction mixture was concentrated at reduced pressure to give the title compound.

Workup

  1. washwashed with saturated bicarbonate solution, water×2 and brine
  2. customDrying
  3. customsolvent evaporation

Sources & evidence

ORD record
ord-068564d098134908867ab906e59a26ac
Source dataset
uspto-grants-2001_11
Patent number
US06319932B1

Reaction notes

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