Sodium Hydroxide → 3-H-epoxybenzazepin

HRID 34288Notes

Reaction equation

HRID 34288 reaction equation
C(O)(=O)C(O)=O.C([N:14]1[CH2:20][CH:19]2[O:21][CH:16]([C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=32)[CH2:15]1)C1C=CC=CC=1.[OH-].[Na+]>CO.[Pd]>[N:14]1[C:15]2[CH:16]=[CH:17][CH:25]=[CH:24][C:23]=2[CH:22]=[CH:18][CH:19]2[O:21][C:20]=12

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 142087323-Benzyl-1,5-epoxy-1,2,4,5-tetrahydro-3-benzazepin oxalate

Product 1

HCID 867423053-H-epoxybenzazepinYield 69.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of the compound prepared in Example 18 (6.1 g, 0.018M) in methanol (300 ml) was hydrogenated (0.61 g, 10% Pd-C) in a Parr apparatus at an initial pressure of 30 psi for 3.5 hours. The resulting solution of the product in methanol was made basic with aqueous NaOH, filtered through Celite and evaporated. The residue was partitioned between H2O and CH2Cl2 ; the organic layer was dried (Na2SO4) to give 3-H-epoxybenzazepin (1.95 g, 68% yield). This compound was treated with acetic anhydride (6 ml) and allowed to stir for two hours. Excess acetic anhydride was removed in vacuo to give 3-acetylepoxybenzazepin as a white solid (2.2 g), mp 126°-128° C. NMR (CDCl3) δ 1.80 ppm (s, 3H, --CH3), 3.10-4.45 (m, 4H, --CH2 --N--CH2), 5.20 [m, 2H, (2x), ArCHO], 7.30 (s, 4H, aromatic H). MS: 203 (M+).

Workup

  1. customfor 3.5 hours
  2. filtrationfiltered through Celite
  3. customevaporated
  4. customThe residue was partitioned between H2O and CH2Cl2
  5. dry with materialthe organic layer was dried (Na2SO4)

Sources & evidence

ORD record
ord-0ad12440f5994e14bad0ca19733a7c36
Source dataset
uspto-grants-1988_08
Patent number
US04761413

Reaction notes

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