Potassium Iodide → 2-Amino-3-carboethoxy-6-(3-phenyl)propyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 325071Notes

Reaction equation

HRID 325071 reaction equation
[NH2:1][C:2]1[S:10][C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:16]1([CH2:22][CH2:23][CH2:24]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[NH2:1][C:2]1[S:10][C:5]2[CH2:6][N:7]([CH2:24][CH2:23][CH2:22][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 212359Thieno(2,3-c)pyridine-3-carboxylic acid, 4,5,6,7-tetrahydro-2-amino-, ethyl ester,

Product 1

HCID 224645562-Amino-3-carboethoxy-6-(3-phenyl)propyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridineYield 51.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.0 g (44.2 mmol) of 2-amino-3-carboethoxy-4,5,6,7-tetra-hydrothieno[2,3-c)pyridine [sic] in 100 ml of toluene were mixed with 9.0 g (45 mM) of 1-phenyl-3-bromopropane, 400 mg of potassium iodide and 6.1 g (44.2 mmol) of finely powdered potassium carbonate and refluxed for 6 h. The residue after concentration in a rotary evaporator was taken up in water, adjusted to pH=10 and extracted twice with methylene chloride. The crude product after drying and concentration of the organic phase was extracted by stirring in 50 ml of isopropanol. The pale solid was filtered off with suction and washed with isopropanol. 7.8 g (51%) of product with melting point 108-110° C. were isolated.

Workup

  1. temperaturerefluxed for 6 h
  2. concentrationThe residue after concentration
  3. customin a rotary evaporator
  4. extractionextracted twice with methylene chloride
  5. dry with materialThe crude product after drying
  6. extractionconcentration of the organic phase was extracted
  7. filtrationThe pale solid was filtered off with suction
  8. washwashed with isopropanol

Sources & evidence

ORD record
ord-343c7c476ae244d18c1c4f74fe4e0b7d
Source dataset
uspto-grants-2001_04
Patent number
US06222034B1

Reaction notes

Loading…