Hydrochloric Acid → 1-[(Cyclohex-1-en-1-yl)methyl]piperidin-4-amine

HRID 446011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446011
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14]C(=O)OC(C)(C)C)[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.Cl.[OH-].[Na+]>CO>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71293652tert-Butyl N-[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamate

Produkt 1

HCID 866782451-[(Cyclohex-1-en-1-yl)methyl]piperidin-4-amineAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl N-[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamate obtained in Example 4a (7.47 g, 25.4 mmol), a 5 N aqueous hydrochloric acid solution (25 ml, 125 mmol) and methanol (100 ml) was stirred at 70° C. for 1.5 hours. The reaction mixture was ice-cooled, a 5 N aqueous sodium hydroxide solution (25 ml, 125 mmol) was added, and the solvent was distilled off. Water was added to the residue, which was extracted with ethyl acetate twice. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off to give the title compound (4.73 g, yield: 95.8%).

Aufarbeitung

  1. temperaturecooled
  2. distillationthe solvent was distilled off
  3. additionWater was added to the residue, which
  4. extractionwas extracted with ethyl acetate twice
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-6f09c634598749af8bcb0300466c69f2
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476301B2

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