Triethylamine → Ethyl 5-benzyl-7,7-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate

HRID 468669Notes

Reaction equation

HRID 468669 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12]([CH3:15])([CH3:14])[C:11](Cl)=[C:10]([CH:17]=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][C:12]([CH3:14])([CH3:15])[C:11]2[S:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 866513211-Benzyl-4-chloro-5,5-dimethyl-1,2,5,6-tetrahydropyridine-3-carbaldehyde

Product 1

HCID 66931877Ethyl 5-benzyl-7,7-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylateYield 34.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl-4-chloro-5,5-dimethyl-1,2,5,6-tetrahydropyridine-3-carbaldehyde (75 g, 0.28 mol) in DCM (1.2 L) was added ethyl 2-mercaptoacetate (67 g, 0.56 mol) and triethylamine (85 g, 0.84 mol) was added slowly at room temperature. Upon complete addition, the reaction mixture was heated at reflux overnight. Upon cooling to room temperature, the reaction was quenched with the addition of water. The organic layer was washed with water, dried over anhydrous Na2SO4, concentrated and purified by silica gel chromatography (0-20% EtOAc/hexane) to afford the title compound (31.7 g, 27.5% over two steps).

Workup

  1. additionwas added slowly at room temperature
  2. additionUpon complete addition
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux overnight
  5. customthe reaction was quenched with the addition of water
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-537780da118c4cbfb449126f28d09b14
Source dataset
uspto-grants-2014_01
Patent number
US08624040B2

Reaction notes

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