Ammonium formate → HCID 12262631, compound

HRID 274078Notes

Reaction equation

HRID 274078 reaction equation
Cl.C([NH:9][CH2:10][C:11]1([OH:23])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=2)[CH2:14][CH2:13][CH2:12]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[NH2:9][CH2:10][C:11]1([OH:23])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=2)[CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 200948371-Benzylaminomethyl-7-methoxy-1,2,3,4-tetrahydro-1-naphthalenol hydrochloride

Product 1

HCID 12262631HCID 12262631, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-benzylaminomethyl-7-methoxy-1,2,3,4-tetrahydro-1-naphthalenol hydrochloride (45.00 g), ammonium formate (25.50 g), and 10% palladium on carbon (50% wet, 4.5 g) in methanol was refluxed for 40 minutes. After cooling, the catalyst was removed by filtration and the filtrate was evaporated in vacuo. Water (45 ml), 1N hydrochloric acid (90 ml) and diethyl ether (120 ml) were added to the residue and the aqueous layer was separated. The aqueous layer was made alkaline with 5N aqueous sodium hydroxide (45 ml), and extracted with ethyl acetate (600 ml×6 times). The organic layers were combined, dried over sodium sulfate, and evaporated in vacuo to give 1-aminomethyl-7-methoxy-1,2,3,4-tetrahydro-1-naphthalenol (27.89 g) as a pale yellow powder.

Workup

  1. temperaturewas refluxed for 40 minutes
  2. temperatureAfter cooling
  3. customthe catalyst was removed by filtration
  4. customthe filtrate was evaporated in vacuo
  5. additionWater (45 ml), 1N hydrochloric acid (90 ml) and diethyl ether (120 ml) were added to the residue
  6. customthe aqueous layer was separated
  7. extractionextracted with ethyl acetate (600 ml×6 times)
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-f86cfbda0d81404998209ec5907867a9
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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