Triethylamine → N-[(1-butyl-2-pyrrolidinyl)methyl]-6-chloro-4-methyl-3,4-dihydro-2H-1,4-benzothiazine-8-carboxamide

HRID 2081556Notes

Reaction equation

HRID 2081556 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][CH2:31][CH:32]1[CH2:36][CH2:35][CH2:34][N:33]1[CH2:37][CH2:38][CH2:39][CH3:40]>C(OCC)(=O)C>[CH2:37]([N:33]1[CH2:34][CH2:35][CH2:36][CH:32]1[CH2:31][NH:30][C:13]([C:4]1[C:5]2[S:10][CH2:9][CH2:8][N:7]([CH3:11])[C:6]=2[CH:12]=[C:2]([Cl:1])[CH:3]=1)=[O:15])[CH2:38][CH2:39][CH3:40]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 108478516-chloro-4-methyl-3,4-dihydro-2H-1,4-benzothiazine-8-carboxylic acidHCID 12829006(1-Butylpyrrolidin-2-YL)methanamine

Product 1

HCID 19780172N-[(1-butyl-2-pyrrolidinyl)methyl]-6-chloro-4-methyl-3,4-dihydro-2H-1,4-benzothiazine-8-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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 1.39 g of 2-aminomethyl-1-butylpyrrolidine at --10° C. 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 residue thus obtained was crystallized from diisopropyl ether. The crystals were collected by filtration and recrystallized from diisopropyl ether to give N-[(1-butyl-2-pyrrolidinyl)methyl]-6-chloro-4-methyl-3,4-dihydro-2H-1,4-benzothiazine-8-carboxamide as colorless crystals. Melting point: 108°-109° 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 residue thus obtained
  7. customwas crystallized from diisopropyl ether
  8. filtrationThe crystals were collected by filtration
  9. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-68104722b94e48cea88bc18d4f38a24c
Source dataset
uspto-grants-1993_02
Patent number
US05185333

Reaction notes

Loading…