Formaldehyde → HCID 54533758, compound

HRID 654886Notes

Reaction equation

HRID 654886 reaction equation
O.Cl.[CH3:3][O:4][C:5]1[C:13]2[O:12][C:11]([CH2:14][NH:15][CH2:16][CH2:17][NH:18][C:19]([C:21]34[CH2:30][CH:25]5[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]5)[CH2:22]3)[CH2:28]4)=[O:20])=[CH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[CH3:31]OC1C2OC(CNCCNC(C34CC5CC(CC(C5)C3)C4)=O)=CC=2C=CC=1.Cl.C=O>C(O)C.[Pd]>[CH3:3][O:4][C:5]1[C:13]2[O:12][C:11]([CH2:14][N:15]([CH3:31])[CH2:16][CH2:17][NH:18][C:19]([C:21]34[CH2:22][CH:23]5[CH2:29][CH:27]([CH2:26][CH:25]([CH2:24]5)[CH2:30]3)[CH2:28]4)=[O:20])=[CH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 131717472HCID 131717472, compound

Product 1

HCID 54533758HCID 54533758, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[2-[[(7-Methoxy-2-benzofuranyl)methyl]amino]ethyl]tricyclo[3.3.1.13,7 ]decane-1-carboxamide hydrochloride hemihydrate (1.0 g, 2.4 mmole), prepared as in Example 2, was dissolved in 100 ml of ethanol and 5 ml of 38% aqueous formaldehyde and 500 mg of 10% palladium on carbon were added. The mixture was hydrogenated at 50 psi on a Parr apparatus for 24 hours. The mixture was then filtered through celite and 300 ml of ether added. It was washed with 100 ml portions of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over sodium sulfate, filtered and evaporated in vacuum. The residue was purified by column chromatography on 100 g of silica gel with chloroform as eluant and recrystallized from acetone/diethyl ether with the addition of 3 ml of 4N HCl/isopropanol to give 560 mg of the title compound as a white solid, monohydrochloride, quarter hydrate, m.p. 156°-158° C.

Workup

  1. filtrationThe mixture was then filtered through celite and 300 ml of ether
  2. additionadded
  3. washIt was washed with 100 ml portions of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuum
  7. customThe residue was purified by column chromatography on 100 g of silica gel with chloroform as eluant
  8. customrecrystallized from acetone/diethyl ether with the addition of 3 ml of 4N HCl/isopropanol

Sources & evidence

ORD record
ord-a726796209804089bdac0c5f8d96b973
Source dataset
uspto-grants-1992_07
Patent number
US05134140

Reaction notes

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