Triethylamine → 6-chloro-4-methyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzothiazine-8-carboxamide

HRID 2081555Notes

Reaction equation

HRID 2081555 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=O)[C:5]2[S:10][CH2:9][CH2:8][N:7]([CH3:11])[C:6]=2[CH:12]=1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[NH2:30][CH:31]1[CH:36]2[CH2:37][CH2:38][N:33]([CH2:34][CH2:35]2)[CH2:32]1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([NH:30][CH:31]2[CH:36]3[CH2:37][CH2:38][N:33]([CH2:34][CH2:35]3)[CH2:32]2)=[O:15])[C:5]2[S:10][CH2:9][CH2:8][N:7]([CH3:11])[C:6]=2[CH:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 1232383-AminoquinuclidineHCID 108478516-chloro-4-methyl-3,4-dihydro-2H-1,4-benzothiazine-8-carboxylic acid

Product 1

HCID 104981616-chloro-4-methyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzothiazine-8-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 1.8 g of 6-chloro-4-methyl-3,4-dihydro-2H-1,4-benzothiazine-8-carboxylic acid in 30 ml of ethyl acetate was added 1.05 g of triethylamine, and then added 0.891 g of pivaloyl chloride dropwise with stirring at -10° C. to -5° C. followed by stirring the mixture at the same temperature for 30 minutes. To the resultant mixture was added a solution of 1.12 g of 3-aminoquinuclidine in 15 ml of ethyl acetate at -10° to -5° C. and then stirred at room temperature for an hour. After the reaction solution was washed with water, dried over anhydrous sodium sulfate and concentrated, the crystalline residue thus obtained was recrystallized from ethyl acetate to give 6-chloro-4-methyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzothiazine-8-carboxamide as yellow crystals. Melting point: 195°-196° C.

Workup

  1. stirringby stirring the mixture at the same temperature for 30 minutes
  2. stirringstirred at room temperature for an hour
  3. washAfter the reaction solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customthe crystalline residue thus obtained
  7. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-23bbd03679e34015a1a68ac0b8217dff
Source dataset
uspto-grants-1993_02
Patent number
US05185333

Reaction notes

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