Phthalylglycine aldehyde → N-(2-Aminoethyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 379523

Reaktionsgleichung

Reaktionsgleichung von HRID 379523
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][CH2:10]2)=[CH:5][CH:4]=1.C1(=O)[N:19](CC=O)[C:18](=O)[C:17]2=CC=CC=C12.CC([O-])=O.[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[NH2:19][CH2:18][CH2:17][N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10]1

Komponenten

6

Edukt 4

HCID 76201Phthalylglycine aldehydeHCID 1796067,8-Dimethoxy-1,2,3,4-tetrahydroisoquinolineHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 15884736N-(2-Aminoethyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinolineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 7,8dimethoxy-1,2,3,4-tetrahydroisoquinoline (421 mg, 2.2 mmol), 2-phthalimidoacetaldehyde (410 mg, 2.2 mmol) and NaOAc (180 mg, 2.2 mmol) in 27 mL of CH2Cl2 was added 690 mg (3.25 mmol) of NaBH(OAc)3 in small portions. After stirring 1 hour at room temperature, the reaction mixture was diluted with CH2Cl2 and washed with a saturated Na2CO3 solution and brine. The residue obtained after evaporation of CH2Cl2 was dissolved in 25 mL of EtOH and treated with 1.2 mL of hydrazine hydrate overnight. The reaction mixture was then filtered and evaporated to give 510 mg (100%) of the title compound; MS m/e 327 (M+1).

Aufarbeitung

  1. washwashed with a saturated Na2CO3 solution and brine
  2. customThe residue obtained
  3. customafter evaporation of CH2Cl2
  4. dissolutionwas dissolved in 25 mL of EtOH
  5. additiontreated with 1.2 mL of hydrazine hydrate overnight
  6. filtrationThe reaction mixture was then filtered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d1c0c9b4ab2b45c485c159650512548b
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300316B1

Verknüpfte Notizen

Wird geladen…