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Sodium Iodide → HCID 58492490, compound

HRID 2047980
Notes
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Reaction equation

HRID 2047980 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:12](=[O:23])[C:11]2[C:6]1=[C:7]([O:27][CH2:28][CH2:29][CH3:30])[CH:8]=[C:9]1[CH2:26][CH2:25][CH2:24][C:10]1=2.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(OCC)(=O)C.O.CN(C)C=O>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[C:12](=[O:23])[C:11]3[C:6](=[C:7]([O:27][CH2:28][CH2:29][CH3:30])[CH:8]=[C:9]4[CH2:26][CH2:25][CH2:24][C:10]4=3)[N:5]([CH2:4][CH2:3][CH2:2][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:14]=2)=[CH:20][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 584923966-(3-Chloropropyl)-8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one

Product 1

HCID 58492490HCID 58492490, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture containing 6-(3-chloropropyl)-8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one (700 mg, 1.64 mmol), morpholine (165 mg, 1.90 mmol), potassium carbonate (341 mg, 2.47 mmol), sodium iodide (295 mg, 1.97 mmol) and dimethyl formamide (3 ml) was stirred at 60° C. for 7 hours. Water and ethyl acetate were added to the reaction mixture, followed by separation. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=70:1→50:1). The purified product was concentrated under reduced pressure to recrystallize the residue from ethyl acetate-n-hexane, giving a white powder of 8-(4-methoxyphenyl)-6-(3-morpholin-4-ylpropyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one (295 mg, yield: 38%).

Workup

  1. customfollowed by separation
  2. washThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified
  5. concentrationThe purified product was concentrated under reduced pressure
  6. customto recrystallize the residue from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-2b2f6af70c0a4414a8025e12b8e0a4b9
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08592593B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes