Piperidine → HCID 10151077, compound

HRID 916974Notes

Reaction equation

HRID 916974 reaction equation
Cl[C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:7]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[CH:6][C:3]=1[C:4]#[N:5].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C1(C)C=CC=CC=1>[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=1[C:8]1[C:7]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)=[CH:6][C:3]([C:4]#[N:5])=[C:2]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[N:9]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 10309275HCID 10309275, compound

Product 1

HCID 10151077HCID 10151077, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To an oven-dried round bottom flask fitted with a rubber septa was added toluene (1 mL), the product of Step D of Example 114 (0.050 g; 0.134 mmol) and piperidine (0.070 mL; 0.670 mmol). The sealed reaction mixture was heated at 100° C. and stirred for 16 hours. The reaction mixture was allowed to cool to room temperature, then it was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic portion was separated and washed with more saturated NaHCO3 solution (2×), brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification was done by MPLC (silica gel; 0-10% ethyl acetate:hexane) to afford the desired product: m/e=422 (M+1) Rt=5.10 min on LCMS.

Workup

  1. customTo an oven-dried round bottom flask fitted with a rubber septa
  2. customThe sealed reaction mixture
  3. temperatureto cool to room temperature
  4. customit was partitioned between ethyl acetate and saturated NaHCO3 solution
  5. customThe organic portion was separated
  6. washwashed with more saturated NaHCO3 solution (2×), brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification

Sources & evidence

ORD record
ord-a0b7fe51f83d4063bf23d6e616e1e28f
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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