1-Naphthalenemethanamine → N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine

HRID 580006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 580006
[C:1]1([CH2:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:13][C:14]([CH3:22])([CH3:21])[C:15]#[C:16][CH:17]=[CH:18][CH:19]=O.[BH4-].[Na+]>C(OCC)C.CO>[CH3:13][C:14]([CH3:22])([CH3:21])[C:15]#[C:16][CH:17]=[CH:18][CH2:19][NH:12][CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 83551-NaphthalenemethanamineHCID 4311764Sodium borohydrideHCID 539349696,6-Dimethyl-2-hepten-4-ynal

Produkt 1

HCID 188542N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 1-naphthalenemethanamine (1.34 g, 8.51 mmol) and 6,6-dimethyl-2-hepten-4-ynal (1.16 g, 8.51 mmol) in 20 ml of dry ethyl ether was stirred over 4A sieves overnight. Sieve material was then removed by centrifugation, washed once with ethyl ether and the combined ether fractions concentrated to afford the crude condensed product. About 8.08 mmol of this material was stirred with sodium borohydride (343 mg, 9.06 mmol) in 20 ml of methanol at room temperature for 3.75 hours. The reaction mixture was partitioned between aqueous sodium bicarbonate and methylene chloride, the aqueous layer extracted twice with methylene chloride, and the combined organic solution washed with water and dried over magnesium sulfate. Removal of the solvent afforded N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine as a mixture of the E and Z isomers. Flash chromatography of this product on silica gel (5 cm column, eluting with 0.2% triethylamine in chloroform) afforded 0.74 g of the pure (E)-N-6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine.

Aufarbeitung

  1. customSieve material was then removed by centrifugation
  2. washwashed once with ethyl ether
  3. concentrationthe combined ether fractions concentrated
  4. customto afford the crude
  5. customcondensed product
  6. customThe reaction mixture was partitioned between aqueous sodium bicarbonate and methylene chloride
  7. extractionthe aqueous layer extracted twice with methylene chloride
  8. washthe combined organic solution washed with water
  9. dry with materialdried over magnesium sulfate
  10. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-035b5a0b6e994094b2b499944d86fded
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04751245

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