Hydrochloric Acid → HCID 20205157, compound

HRID 978172Notes

Reaction equation

HRID 978172 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.[C:10](Cl)(=[O:14])[C:11]([CH3:13])=[CH2:12].[OH-].[Na+].COC1C=CC(O)=CC=1.Cl>>[C:10]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1)(=[O:14])[C:11]([CH3:13])=[CH2:12]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 37734-Piperidinecarboxylic acidHCID 90154-MethoxyphenolHCID 13528Methacryloyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 20205157HCID 20205157, compoundYield 81.3%

Procedure

The procedure of Example A is used in this example. Isonipecotic acid 43 g, (0.33 mol), 39 g (0.39 mol) of methacryloyl chloride, 29.6 g (0.79 mol) of sodium hydroxide and a trace amount of p-methoxyphenol are charged to the reaction vessel. The reaction mixture is run at 0°-5° C. for a period of three hours and acidified with 2N HCl to pH 3.5. White precipitate is formed and extracted with ethyl acetate. The combined organic layer is washed with saturated sodium chloride solution, dried over magnesium sulfate, and evaporated to yield crystalline material which is recrystallized from ethyl acetate, to produce 52.9 g (81%) of the product. Found: melting point 90°-93° C. NMR (CDCl3), 4.9 gamma (s, 1H, =CH2), 4.7 gamma (s, 1H, =CH2), 3.8 gamma (br s, 2H, NCH2), 1.7.

Workup

  1. customWhite precipitate is formed
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer is washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto yield crystalline material which
  7. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-af409070d7324ac385a0a4fc161edea6
Source dataset
uspto-grants-1987_05
Patent number
US04663409

Reaction notes

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