1-(4-Methylbenzyl)piperazine → 1-(2-Methoxyphenyl)-3-(4-methoxyphenylimino)-3-[4-(4-methylbenzyl)-1-piperazinyl]propyne

HRID 1761710

Reaktionsgleichung

Reaktionsgleichung von HRID 1761710
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[C:11]#[CH:12])=[CH:5][CH:4]=1.ClC(Cl)=N[C:30]1[CH:37]=[CH:36][C:33]([O:34][CH3:35])=[CH:32][CH:31]=1.CC1C=CC(CN2CCNCC2)=CC=1.C([Li])CCC.COC1C=CC=CC=1C=C(Br)Br>C(OCC)C.O1CCCC1.CCCCCC>[CH3:35][O:34][C:33]1[CH:36]=[CH:37][CH:30]=[CH:31][C:32]=1[C:12]#[C:11][C:10](=[N:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[N:13]1[CH2:14][CH2:15][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[CH2:17][CH2:18]1

Komponenten

9

Edukt 5

HCID 7647231-(4-Methylbenzyl)piperazineHCID 104244052-Methoxy-beta,beta-dibromostyreneHCID 13381069(4-Methoxyphenyl)carbonimidoylHCID 867430134-Methoxyphenylimino-3-[4-(4-methylbenzyl)-1-piperazinyl]propyneHCID 178418339Butyllithium

Produkt 1

HCID 212420811-(2-Methoxyphenyl)-3-(4-methoxyphenylimino)-3-[4-(4-methylbenzyl)-1-piperazinyl]propyne

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

1-(2-Methoxyphenyl)-3-(4-methoxyphenylimino-3-[4-(4-methylbenzyl)-1-piperazinyl]propyne can be prepared by working as in Example 11 but starting with a solution of N-dichloromethylene-p-anisidine (20.6 g) in ethyl ether (200 cc) to which a solution of 4-(4-methylbenzyl)piperazine (38.4 g) in tetrahydrofuran (150 cc) is added. The solution obtained after filtration is added in the course of 30 minutes at a temperature of about -70° C. to a solution of 2-(2-methoxyphenyl)ethynyllithium obtained by adding, in the course of 20 minutes, at a temperature of about -70° C., a 1.6M solution (126 cc) of butyllithium in hexane to a solution of 2-methoxy-β,β-dibromostyrene (29.5 g) in tetrahydrofuran (300 cc). 1-(2-Methoxyphenyl)-3-(4-methoxyphenylimino)-3-[4-(4-methylbenzyl)-1-piperazinyl]propyne (30.6 g), m.p. 83° C., is thereby obtained.

Aufarbeitung

  1. additionis added
  2. customThe solution obtained
  3. filtrationafter filtration
  4. additionis added in the course of 30 minutes at a temperature of about -70° C. to a solution of 2-(2-methoxyphenyl)ethynyllithium
  5. customobtained
  6. additionby adding, in the course of 20 minutes, at a temperature of about -70° C.

Quellen und Nachweise

ORD-Eintrag
ord-a674f510920647ae85a2d21d0dd06300
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04826974

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