Hydrochloric Acid → HCID 20298469, compound

HRID 1389230Notes

Reaction equation

HRID 1389230 reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.Br[CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17].Cl.C(=O)(O)[O-].[Na+].[CH2:27]([O:29]CC)[CH3:28]>O>[CH:2]1([N:1]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:27](=[O:29])[CH3:28])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 76300Ethyl 4-bromobutyrateHCID 516892Sodium Bicarbonate

Product 1

HCID 20298469HCID 20298469, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

R1 =--CH3, R=1,2,3,4-tetrahydro-1-naphthyl, n=3 14.7 g of 1-amino-1,2,3,4-tetrahydronaphthalene and 9.7 g of ethyl 4-bromobutyrate are stirred together for 48 hours at room temperature. After addition of 200 ml of diethyl ether thereto the resulting precipitate is filtered off, and the filtrate is shaken with dilute hydrochloric acid. The hydrochloric acid extract is neutralized (pH approx. 7) with dilute ammonia solution. The separated oil is taken up in diethyl ether, and the residue (10.9 g), which remains after drying and distilling off the solvent, is taken up in 100 ml of benzene. After the addition of 5.9 g of ethyldiisopropylamine thereto, 3.6 g of acetyl chloride are added slowly and dropwise while stirring. After 3 hours the resulting reaction mixture is mixed with 200 ml of diethyl ether and shaken successively with water, dilute hydrochloric acid and sodium bicarbonate solution. The residue (12.4 g), remaining after drying and distilling off the solvent, is taken up in 100 ml of benzene and mixed with a solution of 3.0 g of potassium hydroxide in 20 ml of ethanol. After 24 hours the mixture is shaken out with water, and the aqueous phase is acidified. The initial oily precipitate is taken up in dichloromethane. After distilling off the solvent, the product crystallizes out after several days. It is recrystallized from a mixture (2:1) of isopropyl alcohol and petrol ether to obtain 7.9 g (57.7% of theory) of 4-[N-(1,2,3,4-tetrahydro-1-naphthyl)acetamido]butyric acid, MP 141° to 142°.

Workup

  1. filtrationthe resulting precipitate is filtered off
  2. extractionThe hydrochloric acid extract
  3. customafter drying
  4. distillationdistilling off the solvent
  5. additionAfter the addition of 5.9 g of ethyldiisopropylamine
  6. addition3.6 g of acetyl chloride are added slowly
  7. stirringdropwise while stirring
  8. customAfter 3 hours the resulting reaction mixture
  9. customafter drying
  10. distillationdistilling off the solvent
  11. additionmixed with a solution of 3.0 g of potassium hydroxide in 20 ml of ethanol
  12. stirringAfter 24 hours the mixture is shaken out with water
  13. distillationAfter distilling off the solvent
  14. customthe product crystallizes out after several days
  15. customIt is recrystallized from a mixture (2:1) of isopropyl alcohol and petrol ether

Sources & evidence

ORD record
ord-9a1472108bef465db5cd994683466f67
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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