HCID 14208763, compound → HCID 14208765, compound

HRID 1722449Notes

Reaction equation

HRID 1722449 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].C([N:14]1[CH2:20][CH:19]2[O:21][CH:16]([C:17]3[CH:25]=[C:24]4[O:26][CH2:27][O:28][C:23]4=[CH:22][C:18]=32)[CH2:15]1)C1C=CC=CC=1>CO.CC(O)=O.[Pd]>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[O:21]1[CH:19]2[C:18]3[CH:22]=[C:23]4[O:28][CH2:27][O:26][C:24]4=[CH:25][C:17]=3[CH:16]1[CH2:15][NH:14][CH2:20]2

Participants

5

Reactant 1

HCID 14208763HCID 14208763, compound

Product 1

HCID 14208765HCID 14208765, compoundYield 46.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of the product prepared in Example 37 (6.6 g, 0.017M) in methanol (200 ml) and AcOH (20 ml) was hydrogenated (10% Pd-C, 0.66 g) in a Parr apparatus at an initial pressure of 40 psi overnight. The resulting solution was filtered through Celite, evaporated, and crystallized from methanol/ether to give the titled compound (2.33 g, 46% yield). The product was recrystallized from methanol/CCl4 and dried in vacuo to give pure product, mp 193°-195° C. (dec). NMR (DMSO-d6) δ 2.70-3.50 (m, 4H, --CH2 --N--CH2), 5.15 [s, 2H, (2×) ArCHO), 5.95 (s, 2H, --OCH2O), 6.95 (s, 2H, aromatic H), 7.25 (m, OH); MS: 205 (M+).

Workup

  1. custompressure of 40 psi overnight
  2. filtrationThe resulting solution was filtered through Celite
  3. customevaporated
  4. customcrystallized from methanol/ether

Sources & evidence

ORD record
ord-62f1b2fd7ecb4177964f37a8ad184835
Source dataset
uspto-grants-1989_08
Patent number
US04855426

Reaction notes

Loading…