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1-[3-(3,4-METHYLENEDIOXYPHENOXY)PROPYL]-4-PHENYL-PIPERAZINE MALEATE synthesis
- Product Name:1-[3-(3,4-METHYLENEDIOXYPHENOXY)PROPYL]-4-PHENYL-PIPERAZINE MALEATE
- CAS Number:82900-57-0
- Molecular formula:C20H24N2O3
- Molecular Weight:340.42
Yield:82900-57-0 92%
Reaction Conditions:
with lithium carbonate in acetonitrile; for 24 h;Heating / reflux;
Steps:
2
EXAMPLE 2 Preparation of 1-benzo[d][1,3]dioxol-5-yloxy-3-[4(4-W-substituted-phenyl)hexahydro-1-pyrazinyl]propane Derivatives General Procedure In a 15 mL balloon containing a mixture of 0.104 g of 2-(3,4-methylenedioxophenyl)-1-yloxy-propanyl mesilate (0.38 mMol), 0.074 g of lithium carbonate (1.00 mMol) in acetonitrile (6 mL), was added 1.05 mMol of phenylpiperazine. The mixture was kept in reflux for 24 hours under vigorous agitation and nitrogen atmosphere. At the end of this time the solution was concentrated in a rotatory evaporator, solubilized in dichloromethane and mixed in a silica gel. The material was chromatografied in a silica gel column eluted with dichloromethane, followed by chloroform supplying the desired compound. 1-benzo[d][1,3]dioxol-5-yloxy-3-(4-phenylhexahydro-1-pyrazinyl)propane solid light beige, 0.121 g (92%), Rf=0.45 (CHCl3:EtOH 5%), p.f.: 80-82° C. RMN 1H (200 MHz, CDCl3): δ 1.96 (qi, J=6.13, 2H, OCH2CH2CH2N); 2.55 (t, J=6.13, 2H, OCH2CH2CH2N); 2.61 (m, 4H, ArNCH2CH2N); 3.21 (m, 4H, ArNCH2CH2N); 3.95 (t, J=6.13 Hz, 2H, OCH2CH2CH2N); 5.88 (s, 2H, OCH2O); 6.32 (dd, J2=8.43 Hz, J3=1.92, 1H, Ar-H-6'); 6.50 (d, J3=1.92 Hz 1H, Ar-H-2'); 6.69 (d, J2=8.43 Hz, 1H, Ar-H-5'); 6.84 (m, N-Ar-H-4); 6.94 (m, N-Ar-H-2 e 6); 7.25 (m, N-Ar-H-3 e 5); RMN 13C (50 MHz, CDCl3): δ 26.6 (NCH2CH2CH2O) 48.9 (ArNCH2CH2N); 53.1 (ArNCH2CH2N); 55.0 (NCH2CH2CH2O); 67.0 (NCH2CH2CH2O); 97.9 (Ar-2'-CH); 100.9 (OCH2O); 105.5 (Ar-5'-CH); 107.7 (Ar-6'-CH); 115.8 (Ar-2 e 6-2CH); 119.5 (Ar-4-CH); 128.9 (Ar-3 e 5-2CH); 141.3 (Ar-4'-C); 148.0 (Ar-3'-C); 151.1 (Ar-1-C-N); 154.0 (Ar-1'-C-O).
References:
US2007/219213,2007,A1 Location in patent:Page/Page column 8
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