Hydrochloric Acid → 1-(prop-2-enoyl)piperidine-4-carboxylic acid

HRID 978173Notes

Reaction equation

HRID 978173 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:13])[CH:11]=[CH2:12].[OH-].[Na+].Cl>>[C:10]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1)(=[O:13])[CH:11]=[CH2:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 37734-Piperidinecarboxylic acidHCID 13140Acryloyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 187027171-(prop-2-enoyl)piperidine-4-carboxylic acidYield 61.5%

Procedure

The procedure of Example A is used with 43 g (0.3 mol) of isonipecotic acid, 31 g (0.3 mol) of acryloyl chloride, 26.6 g (0.66 mol) of sodium hydroxide at 0° C. (ice-salt bath). The reaction mixture is acidified with 2N HCl to pH 3.0 and extracted with ethyl acetate. The organic layer is washed with a sodium chloride solution, dried over magnesium sulfate to dryness to leave a crystalline material which is crystallized from ethyl acetate n-hexane to yield 33.8 g (60%) product. Melting point 109°-110° C. NMR (CDCl3), 5.4-6.9 gamma (br m, 3H, CH2 =CH), 4.0 gamma (br, 2H), 2.1-3.4 gamma (br m, 3H), 1.2-2.1 gamma m, 4H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with a sodium chloride solution
  3. dry with materialdried over magnesium sulfate to dryness
  4. customto leave a crystalline material which
  5. customis crystallized from ethyl acetate n-hexane

Sources & evidence

ORD record
ord-04834b4a2bc24bcea6111879e9c72458
Source dataset
uspto-grants-1987_05
Patent number
US04663409

Reaction notes

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