2-Methoxyethylamine → 8-(4-benzyloxy-phenyl)-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid (2-methoxy-ethyl)-amide

HRID 362555Notes

Reaction equation

HRID 362555 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16](=[O:31])[N:17]3[C:22](=[C:23]([C:25](O)=[O:26])[CH:24]=2)[C:21]2[S:28][CH:29]=[CH:30][C:20]=2[CH:19]=[CH:18]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:36][O:37][CH2:38][CH2:39][NH2:40]>C1(C)C=CC=CC=1>[CH3:36][O:37][CH2:38][CH2:39][NH:40][C:25]([C:23]1[CH:24]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[C:16](=[O:31])[N:17]2[C:22]=1[C:21]1[S:28][CH:29]=[CH:30][C:20]=1[CH:19]=[CH:18]2)=[O:26]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 24386Thionyl ChlorideHCID 193536298-[p-(benzyloxy)phenyl]-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid

Product 1

HCID 566078178-(4-benzyloxy-phenyl)-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid (2-methoxy-ethyl)-amideYield 82.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 0.15 mg (0.35 mmol) of 8-[p-(benzyloxy)phenyl]-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid in 4 ml of toluene was heated at 50° C. for 4 hours with 0.15 ml (2.1 mmol) of thionyl chloride. After removal of all volatile constituents by distillation the residue was suspended in 5 ml of dioxan, treated with 0.06 g (0.76 mmol) of 2-methoxy-ethylamine and stirred at room temperature for 4 hours. After concentration the residue was taken up in dichloromethane, extracted with water and dried with sodium sulphate. Concentration and washing of the residue with ether gave 0.14 g (74%) of 8-(4-benzyloxy-phenyl)-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid (2-methoxy-ethyl)-amide as a yellow solid.

Workup

  1. customAfter removal of all volatile constituents
  2. distillationby distillation the residue
  3. concentrationAfter concentration the residue
  4. extractionextracted with water
  5. dry with materialdried with sodium sulphate
  6. concentrationConcentration
  7. washwashing of the residue with ether

Sources & evidence

ORD record
ord-99655c9d49254af8b2b357c08ded6091
Source dataset
uspto-grants-1999_02
Patent number
US05869500

Reaction notes

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