Hydrochloric Acid → HCID 18705912, compound

HRID 2287876Notes

Reaction equation

HRID 2287876 reaction equation
[CH2:1]([N:4]([CH2:26][CH2:27][CH3:28])[CH:5]1[CH2:25][C:8]2=[CH:9][C:10]3[C:11](=[O:24])[N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:13](=O)[C:14]=3[CH:15]=[C:7]2[CH2:6]1)[CH2:2][CH3:3].Cl>CC(O)=O.[Zn]>[CH2:26]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:25][C:8]2=[CH:9][C:10]3[C:11](=[O:24])[N:12]([CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:13][C:14]=3[CH:15]=[C:7]2[CH2:6]1)[CH2:27][CH3:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18705903HCID 18705903, compound

Product 1

HCID 18705912HCID 18705912, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Using procedure 47, 6-(Dipropylamino)-6,7-dihydro-2-(phenylmethyl)cyclopent[f]isoindole-1,3(2H,5H)-dione (124, 0.41 g, 1.0 mmol) was reduced with Zinc dust (0.65 g, 10.0 mmol) in glacial HOAc (20 mL). Purification on silica gel, eluting with 3:1 hexane/acetone gave an oil that was converted to an HCl salt and recrystallized from EtOAc/MeOH to give 125 as a white solid (m.p. 235-236° C.).

Workup

  1. customPurification on silica gel
  2. washeluting with 3:1 hexane/acetone
  3. customgave an oil that
  4. customrecrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-7452fe1cc3204e83854543d242675535
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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