Dimethylformamide → HCID 18353389, compound

HRID 1250698Notes

Reaction equation

HRID 1250698 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 nmmol), 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. Dying and solvent evaporation gave after flash chromatography (silica gel, ethyl acetate) gave 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 product

Workup

  1. washwashed with saturated bicarbonate solution, water×2 and brine
  2. customDying and solvent evaporation
  3. customgave after flash chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-f171581747c74a78b222647d3fac5e81
Source dataset
uspto-grants-2002_01
Patent number
US06339090B1

Reaction notes

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