HCID 54539996, compound → HCID 19864318, compound

HRID 1199929Notes

Reaction equation

HRID 1199929 reaction equation
[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][N:8]([CH3:12])[CH2:7][CH:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:5]=2[S:4][C:3]=1[CH2:19]O>[Pd].C(O)(=O)C.Cl>[ClH:1].[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][N:8]([CH3:12])[CH2:7][CH:6]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:5]=2[S:4][C:3]=1[CH3:19]

Participants

5

Reactant 1

HCID 54539996HCID 54539996, compound

Product 1

HCID 19864318HCID 19864318, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 3-chloro-2-hydroxymethyl-6-methyl-8-phenyl-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine (0.20 g) and 10% palladium on carbon (50 mg) in acetic acid (2 ml) and concentrated hydrochloric acid (0.1 ml) was hydrogenated at 60 psi for 20 hours. The reaction mixture was filtered, evaporated and the residue chromatographed on silica eluting with 1% methanol-ammonia solution in dichloromethane. The combined fractions were dissolved in ethanolic hydrogen chloride, evaporated and crystallised from ethanol-diethylether to give the title product, m.p. 146° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. customthe residue chromatographed on silica eluting with 1% methanol-ammonia solution in dichloromethane
  4. dissolutionThe combined fractions were dissolved in ethanolic hydrogen chloride
  5. customevaporated
  6. customcrystallised from ethanol-diethylether

Sources & evidence

ORD record
ord-c748c8ee26ab41d5b84773951003dbe0
Source dataset
uspto-grants-1990_02
Patent number
US04904653

Reaction notes

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