Water → HCID 67822213, compound

HRID 1033956Notes

Reaction equation

HRID 1033956 reaction equation
[ClH:1].C([NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:20][CH:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:22][CH2:23][CH3:24])=[CH:15][CH:16]=2)[CH2:11]1)C1C=CC=CC=1.O>C(O)C.[Pd]>[ClH:1].[NH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:20][CH:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:22][CH2:23][CH3:24])=[CH:15][CH:16]=2)[CH2:11]1

Participants

5

Reactant 2

HCID 962WaterHCID 67822124HCID 67822124, compound

Product 1

HCID 67822213HCID 67822213, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-benzylamino-7-(ethoxycarbonylbutan-4-yloxy)tetralin hydrochloride (10.7 g), prepared as described in Example 5, in 95% ethanol (250 ml) and water (25 ml) is hydrogenated at 60° C. and atmospheric pressure using 10% Pd/C (1.2 g) as the hydrogenation catalyst. After 6 hours the catalyst is filtered off, the filtrate is concentrated and the residue is taken up in absolute ethanol and concentrated to dryness a few times. The obtained product is then triturated with ethyl ether and filtered. The residue is crystallized from isopropanol yielding 8 g of the compound indicated in the title. M.p. 131°-133° C.

Workup

  1. customis hydrogenated at 60° C.
  2. filtrationAfter 6 hours the catalyst is filtered off
  3. concentrationthe filtrate is concentrated
  4. concentrationconcentrated to dryness a few times
  5. customThe obtained product is then triturated with ethyl ether
  6. filtrationfiltered
  7. customThe residue is crystallized from isopropanol yielding 8 g of the compound

Sources & evidence

ORD record
ord-77b07cf349ee4f8b95e7e0c48fea8854
Source dataset
uspto-grants-1994_05
Patent number
US05312961

Reaction notes

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