Sodium Iodide → HCID 58492490, compound

HRID 1874035Notes

Reaction equation

HRID 1874035 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

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 962WaterSolventHCID 6228DimethylformamideSolventHCID 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-54febefdc21240429c1d1b982d6deab9
Source dataset
uspto-grants-2012_11
Patent number
US08304546B2

Reaction notes

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