Hydrochloric Acid → 4-Piperidinepropanoic acid, 1-(methoxycarbonyl)-

HRID 1416891Notes

Reaction equation

HRID 1416891 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1.[OH-].[K+].Cl[C:15]([O:17][CH3:18])=[O:16].Cl>>[CH3:18][O:17][C:15]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1)=[O:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 14797Potassium HydroxideHCID 15208063-(Piperidin-4-yl)propanoic acid

Product 1

HCID 102627174-Piperidinepropanoic acid, 1-(methoxycarbonyl)-

Procedure

The solution from step b) was brought to pH 12 with aqueous potassium hydroxide. To this solution was added 21 mL methyl chloroformate (0.27 mol). After the reaction was complete, the solution was brought to pH 1 with 6 N HCl and extracted with dichloromethane. The organic layer was dried with sodium sulfate and the dichloromethane displaced with isopropyl ether. The product was isolated as a solid by filtration. Yield 39 gm, 84%. M.p. 89-90° C.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. customThe product was isolated as a solid by filtration

Sources & evidence

ORD record
ord-6e588fdd4b714be98ae0c6ddbeb33c3c
Source dataset
uspto-grants-1999_06
Patent number
US05916902

Reaction notes

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