Thiophene → 1,2,3,4-Tetrahydro-2-[(4-phenoxy-phenyl)methyl]benzothieno[2,3-c]pyridine

HRID 2298883Notes

Reaction equation

HRID 2298883 reaction equation
Cl.[CH2:2]1[C:7]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH2:5][CH2:4][NH:3]1.[O:15]([C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1C=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:30]([O-])(=O)C.[K+].S1C=CC=C1>CO.[Pd]>[O:15]([C:16]1[CH:17]=[CH:18][C:19]([CH2:30][N:3]2[CH2:4][CH2:5][C:6]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[S:8][C:7]=3[CH2:2]2)=[CH:20][CH:21]=1)[C:22]1[CH:23]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 8030ThiopheneHCID 88060o-PhenoxybenzaldehydeHCID 517044Potassium AcetateHCID 122652651,2,3,4-Tetrahydro-[1]benzothieno[2,3-c]pyridine hydrochloride

Product 1

HCID 183789551,2,3,4-Tetrahydro-2-[(4-phenoxy-phenyl)methyl]benzothieno[2,3-c]pyridineYield 72.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1,2,3,4-tetrahydro-[1]benzothieno[2,3-c]pyridine hydrochloride (1:1) (0.01 mol) and phenoxybenzaldehyde (0.01 mol) in methanol (150 ml) was hydrogenated at 50° C. with Pd/C 10% (1 g) as a catalyst in the presence of potassium acetate (2 g) and thiophene 4% (1 ml). After uptake of H2 (1 equiv), the catalyst was filtered off and the filtrate was evaporated. The residue was crystallized from CH3CN, filtered off and dried. This fraction (3 g) was stirred in water with a little NH4OH, and this mixture was extracted with CH2Cl2. The separated organic layer was dried (MgSO4), filtered and the solvent evaporated. The residue was crystallized from CH3CN, filtered off and dried, yielding 2.7 g of 1,2,3,4-tetrahydro-2-[(4-phenoxy-phenyl)methyl]benzothieno[2,3-c]pyridine (compound 34).

Workup

  1. filtrationAfter uptake of H2 (1 equiv), the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from CH3CN
  4. filtrationfiltered off
  5. customdried
  6. extractionthis mixture was extracted with CH2Cl2
  7. dry with materialThe separated organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. customThe residue was crystallized from CH3CN
  11. filtrationfiltered off
  12. customdried

Sources & evidence

ORD record
ord-7220be9bf79a4edf8c2bea286cb196b1
Source dataset
uspto-grants-2002_12
Patent number
US06495555B1

Reaction notes

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