Acetic Acid → 3-Acetyl-1-(1,3-dioxolan-2-yl)-1,5-epoxy-1,2,4,5-tetrahydro-3-benzazepin

HRID 1722445Notes

Reaction equation

HRID 1722445 reaction equation
[CH2:1]([N:8]1[CH2:14][C:13]2([CH:16]3[O:20][CH2:19][CH2:18][O:17]3)[O:15][CH:10]([C:11]3[CH:24]=[CH:23][CH:22]=[CH:21][C:12]=32)[CH2:9]1)[C:2]1C=CC=CC=1.C(O)(=[O:27])C>C(O)C.[Pd]>[C:1]([N:8]1[CH2:14][C:13]2([CH:16]3[O:20][CH2:19][CH2:18][O:17]3)[O:15][CH:10]([C:11]3[CH:24]=[CH:23][CH:22]=[CH:21][C:12]=32)[CH2:9]1)(=[O:27])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 14208754HCID 14208754, compound

Product 1

HCID 142087563-Acetyl-1-(1,3-dioxolan-2-yl)-1,5-epoxy-1,2,4,5-tetrahydro-3-benzazepinYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 10% Pd-C (1.42 g) in a solution of the product from Example 29 (9.75 g, 0.0302M) and glacial acetic acid (12 ml) in absolute ethanol (130 ml) was hydrogenated in a Parr apparatus at an initial pressure of 32 psi. After six hours, the catalyst was removed by filtration through Celite and the solvents removed in vacuo. The residue was taken up in CH2Cl2 (50 ml) and treated with acetic anhydride (6.0 ml). After 15 minutes, the mixture was evaporated to dryness and the residue crystallized from Et2O to give the titled compound (7.34 g. 88% yield) as white crystals, mp 122°-123° C. NMR (CDCl3) δ 1.73 ppm (s, 3H, COCH3), 3.0-4.60 (m, 8H, ##STR46## and --OCH2CH2O--), 5.17 (m, 2H, ##STR47## 7.25 (m, 4H, aromatic H). IR (KBr): 1635 cm-1 (C=O). MS: 275 (M+).

Workup

  1. customthe catalyst was removed by filtration through Celite
  2. customthe solvents removed in vacuo
  3. additiontreated with acetic anhydride (6.0 ml)
  4. waitAfter 15 minutes
  5. customthe mixture was evaporated to dryness
  6. customthe residue crystallized from Et2O

Sources & evidence

ORD record
ord-f3dc4e8344ea4e7fa2d219c2defdcb2e
Source dataset
uspto-grants-1989_08
Patent number
US04855426

Reaction notes

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