N,N-Dimethylaniline → 2-(4-chlorophenyl)-4-(dimethylamino)acetyl-3,4-dihydro-2H-1,4-benzothiazine hydrochloride

HRID 5825

Reaction equation

HRID 5825 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[S:9]2)=[CH:4][CH:3]=1.CN(C)C1C=CC=CC=1.Cl.[CH3:28][N:29]([CH2:31][C:32](Cl)=[O:33])[CH3:30].C(=O)([O-])O.[Na+]>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][N:12]([C:32](=[O:33])[CH2:31][N:29]([CH3:30])[CH3:28])[C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[S:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 516892Sodium BicarbonateHCID 130715242-(4-chlorophenyl)-3,4-dihydro2H-1,4-benzothiazineHCID 139949912-(Dimethylamino)acetyl chloride hydrochloride

Product 1

HCID 197942362-(4-chlorophenyl)-4-(dimethylamino)acetyl-3,4-dihydro-2H-1,4-benzothiazine hydrochlorideYield 165.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine (0.52 g) and N,N-dimethylaniline (0.97 g) in methylene chloride (15 ml) is added dimethylaminoacetyl chloride hydrochloride (0.63 g) under ice cooling, and the mixture is stirred at the same temperature for 2.5 hours. To the reaction mixture is added aqueous sodium hydrogen carbonate solution, and is extracted with chloroform. The chloroform layer is washed, dried and distilled to remove the solvent. The residue is treated with hydrochloric acid and the resulting salt is recrystallized from ethanol-ether to give 2-(4-chlorophenyl)-4-(dimethylamino)acetyl-3,4-dihydro-2H-1,4-benzothiazine hydrochloride (0.63 g, yield 86%).

Workup

  1. extractionis extracted with chloroform
  2. washThe chloroform layer is washed
  3. customdried
  4. distillationdistilled
  5. customto remove the solvent
  6. additionThe residue is treated with hydrochloric acid
  7. customthe resulting salt is recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-1147dbdc36ea4a6199a9f7a5bb454589
Source dataset
uspto-grants-1993_09
Patent number
US05246929

Linked notes

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