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

HRID 704580

Reaction equation

HRID 704580 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-151d200451404f31b9ba084a84df4a28
Source dataset
uspto-grants-1991_01
Patent number
US04988699

Linked notes

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