Hydrochloric Acid → HCID 19372036, compound

HRID 129658Notes

Reaction equation

HRID 129658 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:21])([CH3:20])[C:16]([O:18][CH3:19])=[O:17])C(=O)C2=CC=CC=C12.O.NN.Cl.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:21])([CH3:20])[C:16]([O:18][CH3:19])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 10340Sodium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 19372075HCID 19372075, compound

Product 1

HCID 19372036HCID 19372036, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 15.4 g of methyl 11-phthalimido-2,2-dimethylundecanoate and 2.33 cm3 of 98% hydrazine hydrate in 500 cm3 of methanol is stirred for 12 hours at a temperature in the region of 20° C. 32 cm3 of 5N methanolic hydrochloric acid are added. The solvent is evaporated under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. The residue is taken up in 150 cm3 of distilled water. After stirring for 20 minutes, the solid is separated by filtration and washed with a total of 90 cm3 of distilled water. The aqueous phase is brought to a pH in the region of 9-10 by means of a 10% sodium carbonate solution, extracted with a total of 500 cm3 of diisopropyl ether, dried over magnesium sulphate and then concentrated under reduced pressure (2.7 kPa) at a3 temperature in the region of 40° C. The residue is taken up in a mixture of 15 cm3 of methanol and 50 cm3 of diethyl ether. 10 cm3 of 5N methanolic hydrochloric acid are added and the mixture is evaporated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C. The yellow oil obtained is taken up in 100 cm3 of distilled water. 2 cm3 of 4N hydrochloric acid are added and the mixture is then brought to a pH in the region of 9-10 by means of a 10% sodium carbonate solution. Extraction is carried out with a total of 450 cm3 of ethyl acetate. The organic phase is dried over magnesium sulphate and then concentrated to dryness under reduced pressure (13.5 Pa) at a temperature in the region of 40° C. 6.8 g of methyl 11-amino-2,2-dimethylundecanoate are thus obtained in the form of a viscous yellow oil [Rf =0.54; silica thin layer chromatography; eluent: chloroform/methanol/28% aqueous ammonia 24/6/1 (by volume)].

Workup

  1. customThe solvent is evaporated under reduced pressure (2.7 kPa) at a temperature in the region of 40° C
  2. customthe solid is separated by filtration
  3. washwashed with a total of 90 cm3 of distilled water
  4. extractionextracted with a total of 500 cm3 of diisopropyl ether
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure (2.7 kPa) at a3 temperature in the region of 40° C
  7. additionThe residue is taken up in a mixture of 15 cm3 of methanol and 50 cm3 of diethyl ether
  8. addition10 cm3 of 5N methanolic hydrochloric acid are added
  9. customthe mixture is evaporated to dryness under reduced pressure (2.7 kPa) at a temperature in the region of 40° C
  10. customThe yellow oil obtained
  11. extractionExtraction
  12. dry with materialThe organic phase is dried over magnesium sulphate
  13. concentrationconcentrated to dryness under reduced pressure (13.5 Pa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-a15710d44b1c4173930d9d99de353378
Source dataset
uspto-grants-1995_11
Patent number
US05468888

Reaction notes

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