Hydrogen Bromide → HCID 19709989, compound

HRID 725896Notes

Reaction equation

HRID 725896 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[O:9][C:10]3[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)[CH2:4][CH2:3]1.CO.Br>[Pt](=O)=O.O>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[O:9][C:10]3[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 887MethanolHCID 19710009HCID 19710009, compound

Product 1

HCID 19709989HCID 19709989, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 962WaterSolvent

Procedure

A mixture of 1-methyl-4-(7-methoxy-2-benzofuranyl)-1,2,3,6-tetrahydropyridine (58.0 g), methanol (1.5 l), water (200 ml), 48% HBr (42.0 g), and platinum dioxide were shaken under hydrogen at room temperature for 6 hours. The mixture was filtered; the filtrate was concentrated in vacuo to the aqueous phase, neutralized with 5% Na2CO3 and extracted with CH2 Cl2. The organic phase was washed with water, dried (Na2 SO4) and concentrated in vacuo to give 59 g of the crude product, which was crystallized from methanol/water, m.p. 74°-75° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo to the aqueous phase
  3. extractionextracted with CH2 Cl2
  4. washThe organic phase was washed with water
  5. customdried (Na2 SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5da05f9b24c4471a749a8ce81818d4a
Source dataset
uspto-grants-1998_01
Patent number
US05708007

Reaction notes

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