Reaktion #2315645

Reaktionsgleichung

acetic acid

N-(1,2,3,4-tetrahydro-1-naphthalenyl)homopiperazine

acetone

sodium cyanoborohydride

→

title compound

Ausbeute 99.8%

1-Isopropyl-4-(1,2,3,4-tetrahydro-1-naphthalenyl)homopiperazine

Ausbeute 99.8%

Lösungsmittel

CH3OH

CHCl3

THF

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe content of the flask was then concentrated in vacuo
2. 2
   workup.ADDITIONThe residue was treated with aqueous sodium bicarbonate
3. 3
   Extraktionextracted several times with ethyl acetate which
4. 4
   Trocknenwas then dried with sodium sulphate
5. 5
   FiltrationFiltration and removal of solvent in vacuo
6. 6
   Sonstigegave an oil which
7. 7
   workup.WAITwas subjected to high vacuum for four hours at ambient temperature

Vorschrift

A 100 ml 3-necked flask under nitrogen atmosphere was charged sequentially with N-(1,2,3,4-tetrahydro-1-naphthalenyl)homopiperazine (0.73 g; 3.2 mmol) in THF (20 ml), methanol (10 ml) and acetone (3.3 ml; 45 mmol). To this stirred solution, sodium cyanoborohydride (0.30 g; 4.75 mmol) was added as a solid followed by acetic acid (0.24 ml; 4.2 mmol). After stirring at ambient temperature for 45 minutes, tlc analysis (silica gel, 9:1 CHCl3:CH3OH) of an aliquot revealed the absence of starting amine (Rf 0.03) and the presence of a major component with Rf 0.16. The content of the flask was then concentrated in vacuo. The residue was treated with aqueous sodium bicarbonate and extracted several times with ethyl acetate which was then dried with sodium sulphate. Filtration and removal of solvent in vacuo gave an oil which was subjected to high vacuum for four hours at ambient temperature to yield the title compound (0.87 g); tlc (ibid), homogeneous, Rf 0.16; 1H nmr δ 1.01-1.05 (6H), 3.88-3.92 (m, 1H), 6.98-7.22 (m, 3H), 7.77-7.79 (1, H). Anal: Calcd. for C18H28N2; C, 79.36; H, 10.36; N, 10.28. Found: C, 79.46; H, 10.12; N, 10.08.

Quelle