2-[4-(3-Chloro-propoxy)-phenyl]-imidazo[1,2-a]pyridine → 2-[4-(3-Chloro-propoxy)-phenyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

HRID 1824528Notes

Reaction equation

HRID 1824528 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]3[CH:20]=2)=[CH:8][CH:7]=1>C(O)C.CO.[Pt](=O)=O>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH2:19][CH2:18][CH2:17][CH2:16][N:15]3[CH:20]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 1

HCID 140970942-[4-(3-Chloro-propoxy)-phenyl]-imidazo[1,2-a]pyridine

Product 1

HCID 220156272-[4-(3-Chloro-propoxy)-phenyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridineYield 96.4%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a Parr bottle charged with a mixture of platinum (IV) oxide (30 mg) in ethanol (3 mL) was added a solution of the product of Step A (90 mg) in methanol (6 ml). The mixture was hydrogenated at 40 psi for 4 hours and filtered through a Celite pad which was rinsed with several additional milliliters of methanol and ethanol. The filtrate was collected and evaporated in vacuo to yield the title compound (88 mg) which was used without further purification.

Workup

  1. filtrationfiltered through a Celite pad which
  2. washwas rinsed with several additional milliliters of methanol and ethanol
  3. customThe filtrate was collected
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5c158fe866b1484aa1daaba47b066571
Source dataset
uspto-grants-2006_05
Patent number
US07041828B2

Reaction notes

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