Formic Acid → HCID 15163137, compound

HRID 1110047Notes

Reaction equation

HRID 1110047 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)=O>C(O)C.[OH-].[OH-].[Pd+2]>[NH:8]1[CH2:13][CH2:12][C:11]2([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 15163136HCID 15163136, compound

Product 1

HCID 15163137HCID 15163137, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 1'-benzylspiro[6,7,8,9-tetrahydro-5H-benzocyclohepten-5,4'-piperidine] (526 mg, 1.7 mmol) in ethanol (100 ml), containing formic acid (6 ml), was hydrogenated at 50 p.s.i. in the presence of palladium hydroxide on carbon (Pearlman's catalyst) (250 mg, 50% (w/w)) for 6 hours. The solution was filtered and the solvents removed in vacuo. The residue was taken up in ethyl acetate (50 ml) and washed with 10% (w/v) potassium hydroxide in water (50 ml). The organic phase was separated and the aqueous layer extracted once more with ethyl acetate (50 ml). The combined organic layers were dried (MgSO4) and the solvents removed in vacuo to give spiro [6,7,8,9-tetrahydro-5H-benzocyclohepten-5,4'-piperidine] (240 mg, 65%), which was used without further purification.

Workup

  1. filtrationThe solution was filtered
  2. customthe solvents removed in vacuo
  3. washwashed with 10% (w/v) potassium hydroxide in water (50 ml)
  4. customThe organic phase was separated
  5. extractionthe aqueous layer extracted once more with ethyl acetate (50 ml)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-83e8ab6e36b84541b58b3f0c9b9fb29f
Source dataset
uspto-grants-1994_06
Patent number
US05324733

Reaction notes

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