Hydrochloric Acid → HCID 76754946, compound

HRID 1516455Notes

Reaction equation

HRID 1516455 reaction equation
[F:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([NH2:11])[CH:3]=1.Cl.N([O-])=O.[Na+].[Cl-].F[C:19]1[C:23]2C=CC=[CH:27][C:22]=2[O:21][C:20]=1[N+:28]#N.C([O-])([O-])=O.[Na+].[Na+].C(OC(C1CC(C)C[NH:43]C1=O)=O)C.[OH-].[K+]>O.C(O)(=O)C>[F:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([NH:11][N:43]=[C:19]2[CH2:23][CH2:22][CH2:27][NH:28][C:20]2=[O:21])[CH:3]=1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 152578183-Piperidinecarboxylic acid, 5-methyl-2-oxo-, ethyl esterHCID 23668193Sodium NitriteHCID 58307563HCID 58307563, compoundHCID 86654437HCID 86654437, compound3×

Product 1

HCID 76754946HCID 76754946, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

Fluoro-benzo-furan-amine 8 (1.0 g, 6.527 mmol) was suspended with water (12.55 mL) and concentrated HCl (1.5 mL) was added. The mixture was cooled in an ice bath and a solution of 200 mg NaNO2 in water (12.55 mL) was added dropwise and the mixture was stirred for 30 min. The pH of the solution (Solution A) was adjusted to 4.5 with a 10% solution of Na2CO3. Ethyl-2-oxo-5-methylpiperidine-3-carboxylate (1.19 g, 6.527 mmol) was dissolved in water (12.55 mL) containing potassium hydroxide (0.35 g, 6.25 mmol). The solution was stirred at room temperature overnight. This solution was then cooled in an ice bath and was treated with a solution of fluoro-benzo-furan diazonium chloride (Solution A). The pH of the resulting solution was adjusted to pH 5 by the addition of acetic acid. Stirring was continued for 4 h at 0° C. and kept overnight at freeze. The solid obtained was filtered to yield the desired compound 9 (500 mg, yield 29%).

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled in an ice bath
  3. stirringThe solution was stirred at room temperature overnight
  4. temperatureThis solution was then cooled in an ice bath
  5. stirringStirring
  6. waitwas continued for 4 h at 0° C.
  7. waitkept overnight at freeze
  8. customThe solid obtained
  9. filtrationwas filtered

Sources & evidence

ORD record
ord-61053ad8f445414c84960f1390fe1540
Source dataset
uspto-grants-2012_07
Patent number
US08227501B2

Reaction notes

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