Aluminum;lithium;tetrachloride → (+/-)-6-[(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)methyl]-4,5,6,7-tetrahydro-2-benzothiazolamine

HRID 704580

Reaktionsgleichung

Reaktionsgleichung von HRID 704580
[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Al+3].[Li+].[Cl-].[Cl-].[Cl-].[NH2:11][C:12]1[S:13][C:14]2[CH2:20][CH:19]([C:21]([N:23]3[CH2:28][CH:27]=[C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:25][CH2:24]3)=O)[CH2:18][CH2:17][C:15]=2[N:16]=1>C(OCC)C.O1CCCC1>[C:29]1([C:26]2[CH2:27][CH2:28][N:23]([CH2:21][CH:19]3[CH2:18][CH2:17][C:15]4[N:16]=[C:12]([NH2:11])[S:13][C:14]=4[CH2:20]3)[CH2:24][CH:25]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

6

Edukt 3

HCID 166981Aluminum;lithium;tetrachlorideHCID 6451240Aluminum(III) ChlorideHCID 15101105(+/-)-1-[(2-Amino-4,5,6,7-tetrahydro-6-benzothiazolyl)-carbonyl]-1,2,3,6-tetrahydro-4-phenylpyridine

Produkt 1

HCID 15101109(+/-)-6-[(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)methyl]-4,5,6,7-tetrahydro-2-benzothiazolamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

An ice-cold solution of aluminum chloride (0.80 g) in 20 ml of diethyl ether is added dropwise to a suspension of lithium aluminum chloride (0.65 g) in 30 ml of tetrahydrofuran and 30 ml of diethyl ether under nitrogen. The mixture is stirred at room temperature for 15 minutes and a solution of (±)-1-[(2-amino-4,5,6,7-tetrahydro-6-benzothiazolyl)-carbonyl]-1,2,3,6-tetrahydro-4-phenylpyridine (3.5 g) (Example 6a) in 50 ml of tetrahydrofuran is added dropwise. The reaction mixture is stirred at 40° C. for 30 minutes. After cooling in an ice bath, the reaction is quenched by careful addition of 4 ml of a 10% solution of hydrochloric acid, 4 ml of a 30% solution of sodium hydroxide and 4 ml of water. The salts that precipitate are filtered through Celite and the filtrate evaporated and purified by MPLC (silica; 5% methanol, 95% dichloromethane). The title compound is obtained as a beige solid; mp 187° -190° C.

Aufarbeitung

  1. stirringThe reaction mixture is stirred at 40° C. for 30 minutes
  2. temperatureAfter cooling in an ice bath
  3. customthe reaction is quenched by careful addition of 4 ml of a 10% solution of hydrochloric acid, 4 ml of a 30% solution of sodium hydroxide and 4 ml of water
  4. filtrationThe salts that precipitate are filtered through Celite
  5. customthe filtrate evaporated
  6. custompurified by MPLC (silica; 5% methanol, 95% dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-151d200451404f31b9ba084a84df4a28
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04988699

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