Potassium Carbonate → HCID 58576476, compound

HRID 511146Notes

Reaction equation

HRID 511146 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:23]=[C:22](F)[CH:21]=[CH:20][C:17]=1[C:18]#[N:19].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:22]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([Cl:15])[CH:23]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1090002-Chloro-4-fluorobenzonitrileHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 58576476HCID 58576476, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (427 mg; 2.13 mmol), 2-chloro-4-fluoro-benzonitrile (302 mg; 1.94 mmol) and potassium carbonate (1.07 g; 7.76 mmol) is diluted in dimethylsulfoxide (5 mL) and is heated to 120° C. for 7 hours. After cooling to room temperature, the mixture is diluted with dichloromethane (50 mL) and is filtered. The filtrate is washed with 1N aq. hydrochlorid acid (2×15 mL), with water (20 mL) is then dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product is finally purified by column chromatography on silica gel (dichloromethane:methanol 1:0 and then 98:2) to afford the desired product (290 mg; 0.87 mmol).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationis filtered
  3. washThe filtrate is washed with 1N aq. hydrochlorid acid (2×15 mL), with water (20 mL)
  4. dry with materialis then dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is finally purified by column chromatography on silica gel (dichloromethane:methanol 1:0

Sources & evidence

ORD record
ord-fe3856a12e0644fb9d83f53975182b45
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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