ChemicalBook CAS DataBase List 1-[3-(3,4-METHYLENEDIOXYPHENOXY)PROPYL]-4-PHENYL-PIPERAZINE MALEATE

1-[3-(3,4-METHYLENEDIOXYPHENOXY)PROPYL]-4-PHENYL-PIPERAZINE MALEATE synthesis

4synthesis methods

Product Name:1-[3-(3,4-METHYLENEDIOXYPHENOXY)PROPYL]-4-PHENYL-PIPERAZINE MALEATE
CAS Number:82900-57-0
Molecular formula:C20H24N2O3
Molecular Weight:340.42

92-54-6 Synthesis

92-54-6
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1-Propanol, 3-(1,3-benzodioxol-5-yloxy)-, 1-methanesulfonate

247228-35-9
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1-[3-(3,4-METHYLENEDIOXYPHENOXY)PROPYL]-4-PHENYL-PIPERAZINE MALEATE

82900-57-0
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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).