Hydrochloric Acid → HCID 18705835, compound

HRID 2287881Notes

Reaction equation

HRID 2287881 reaction equation
[CH2:1]([N:4]([CH2:27][CH2:28][CH3:29])[CH:5]1[CH2:26][C:8]2=[CH:9][C:10]3[C:11](=[O:25])[N:12]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([F:24])=[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]>[CH2:27]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:26][C:8]2=[CH:9][C:10]3[C:11](=[O:25])[N:12]([CH2:17][C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=4)[CH2:13][C:14]=3[CH:15]=[C:7]2[CH2:6]1)[CH2:28][CH3:29]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18705808HCID 18705808, compound

Product 1

HCID 18705835HCID 18705835, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Using procedure 47, 6-(dipropylamino)-2-[(4-fluorophenyl)methyl]-6,7-dihydrocyclopent[f]isoindole-1,3(2H,5H)-dione (101, 0.56 g, 1.43 mmol) was reduced with Zinc dust (0.94 g, 14.3 mmol) in glacial HOAc (20 mL). Purification using silica gel, eluting with 9:1 CH2Cl2 /MeOH, afforded an oil that was converted to an HCl salt and recrystallized from EtOAc/MeOH to give 132 as a white solid (m.p. 227-228° C.).

Workup

  1. customPurification
  2. washeluting with 9:1 CH2Cl2 /MeOH
  3. customafforded an oil that
  4. customrecrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-dd4ced874fbb46749a32ff782c1844aa
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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