Piperidine → HCID 59314200, compound

HRID 1047940Notes

Reaction equation

HRID 1047940 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[C:23](F)=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].O1CCOCC1.[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[C:23]([N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 312751,4-DioxaneHCID 59314190HCID 59314190, compound

Product 1

HCID 59314200HCID 59314200, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 10 mL microwave reaction vessel is charged with 2-[(3-fluoro-pyridine-2-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (359, 488 mg, 1.49 mmol), 1,4-dioxane (1.5 mL) and piperidine (1.51 mL, 15.23 mmol). A stirring bar is added. The reaction vial is crimped sealed. The reaction vial is placed in a Smith Microwave reaction apparatus. The temperature is set for 150° C. with a fixed hold time of 10 min. Pre-stir time is set for 20 sec. The reaction vial is removed from the apparatus. The stirring bar is extracted. The contents of the flask are transferred to a round bottom flask and the solvent removed under reduced pressure. Pumping to a constant weight gives 1.02 g of off white solid. This is dissolved in DCM (10 mL) and applied to an ISCO Companion that is fitted with a 40 g column (silica). The column is eluted with EtOAc/heptanes (5%) for 4 column volumes followed by a linear gradient to 65% EtOAc/heptanes over 10 column volumes and then 90% EtOAc/heptanes for 2 column volumes. 14 mL fractions of UV Active eluent are collected. Fractions 2-10 are combined and evaporated by pumping to constant weight to give white solid (0.5 g, 86%).

Workup

  1. additionA stirring bar is added
  2. customThe reaction vial is crimped sealed
  3. customThe reaction
  4. customvial is placed in a Smith Microwave reaction apparatus
  5. customis set for 150° C. with a fixed hold time of 10 min
  6. customThe reaction
  7. customvial is removed from the apparatus
  8. extractionThe stirring bar is extracted
  9. customThe contents of the flask are transferred to a round bottom flask
  10. customthe solvent removed under reduced pressure
  11. customgives 1.02 g of off white solid
  12. customis fitted with a 40 g column (silica)
  13. washThe column is eluted with EtOAc/heptanes (5%) for 4 column volumes
  14. custom14 mL fractions of UV Active eluent are collected
  15. customevaporated

Sources & evidence

ORD record
ord-8d388773abcc43288a63391ec2fad5aa
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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