N-[6-(hydroxymethyl)-1-isoquinolinyl]benzamide → 2,3,4,5-Tetrahydro-1,4-benzoxazepine

HRID 2304278Notes

Reaction equation

HRID 2304278 reaction equation
C([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.OCC1C=C2C(=CC=1)C(NC(=O)C1C=CC=CC=1)=NC=C2>C(O)C.[Pd]>[O:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[CH2:14][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 22665633N-[6-(hydroxymethyl)-1-isoquinolinyl]benzamideHCID 226659024-Benzyl-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine

Product 1

HCID 218827752,3,4,5-Tetrahydro-1,4-benzoxazepine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10.2 g of 4-benzyl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine were dissolved in 100 mL of ethanol and hydrogenated for 5 hours at room temperature using 1.2 g of palladium (10% on carbon) as catalyst. Filtration followed by removal of the solvent in vacuo gave 6. 1g of 2,3,4,5-tetrahydro-benzo[f][1,4j]oxazepine as an oil. EI-MS: 149 (M+).

Workup

  1. filtrationFiltration
  2. customfollowed by removal of the solvent in vacuo
  3. customgave 6

Sources & evidence

ORD record
ord-b0ede0561d45497982ad6cff868187e6
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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