HCID 20269005, compound → 3,4,5,6-Tetrahydro-1-benzazocin-2(1H)-one

HRID 2417840Notes

Reaction equation

HRID 2417840 reaction equation
C(O[CH:5]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9](=[O:17])[CH2:8][CH2:7][CH2:6]1)(=O)C>C(O)C.[Pd]>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1=[O:17]

Participants

4

Reactant 1

HCID 20269005HCID 20269005, compound

Product 1

HCID 124339533,4,5,6-Tetrahydro-1-benzazocin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 6-acetoxy-3,4,5,6-tetrahydro-1-benzazocin-2(1H)-one (7.4 g) in ethanol (250 ml) is hydrogenated at 45 psi at 70° C. using 10% palladium on charcoal (1.5 g) as catalyst. The catalyst is filtered off and the solvent removed under reduced pressure. The residue is recrystallized from methanol/ethyl acetate to give 3,4,5,6-tetrahydro-1-benzazocin-2(1H)-one.

Workup

  1. customis hydrogenated at 45 psi at 70° C.
  2. filtrationThe catalyst is filtered off
  3. customthe solvent removed under reduced pressure
  4. customThe residue is recrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-1c0183dbf2c84d58b0d2ea8fca186e74
Source dataset
uspto-grants-1984_09
Patent number
US04470988

Reaction notes

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