5-Aminovaleric acid → HCID 10427381, compound

HRID 2248568Notes

Reaction equation

HRID 2248568 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23].[OH-].[Na+].O1CCCC1>O>[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1385-Aminovaleric acidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 10377881HCID 10377881, compound

Product 1

HCID 10427381HCID 10427381, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.8 g of 4-piperidinylbenzenesulphonyl chloride are added to a solution comprising 3.51 g of 5-aminovaleric acid and 3.6 g of sodium hydroxide dissolved in 35 cm3 of water, followed by the addition of 35 cm3 of tetrahydrofuran in order to obtain a solution. The temperature rises to 35° C. The mixture is kept stirring for 4 hours at room temperature, the tetrahydrofuran is evaporated off, the reaction medium is acidified using acetic acid, diluted with 100 cm3 of water and extracted with chloroform, the organic phase is dried and the solvents are removed under reduced pressure. 5.8 g of expected product are obtained. M.p. 115°-120° C. After crystallization in an isopropanol/water mixture (1:1), the product, melting point 120°-122° C., is obtained.

Workup

  1. customto obtain a solution
  2. customrises to 35° C
  3. customthe tetrahydrofuran is evaporated off
  4. additiondiluted with 100 cm3 of water
  5. extractionextracted with chloroform
  6. customthe organic phase is dried
  7. customthe solvents are removed under reduced pressure

Sources & evidence

ORD record
ord-ddc3de11d0744bf185201636b616ea14
Source dataset
uspto-grants-1991_08
Patent number
US05041436

Reaction notes

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