Methyl iodide → HCID 86753188, compound

HRID 398762Notes

Reaction equation

HRID 398762 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[C@H:11]([C:12]2[CH:17]=[CH:16][C:15]3[O:18][CH2:19][O:20][C:14]=3[CH:13]=2)[CH2:10][C:9]2[CH:21]=[CH:22][CH:23]=[CH:24][C:8]=2[NH:7][C:6]1=[O:25])=[O:4].[H-].[Na+].CI.[C:30](OCC)(=O)C.CCCCCC>CN(C=O)C>[CH3:1][O:2][C:3]([C@H:5]1[C@H:11]([C:12]2[CH:17]=[CH:16][C:15]3[O:18][CH2:19][O:20][C:14]=3[CH:13]=2)[CH2:10][C:9]2[CH:21]=[CH:22][CH:23]=[CH:24][C:8]=2[N:7]([CH3:30])[C:6]1=[O:25])=[O:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21226206Ethyl acetate hexaneHCID 86753189HCID 86753189, compound

Product 1

HCID 86753188HCID 86753188, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (+/-)-Trans-1,3,4,5-tetrahydro-3-(methoxycarbonyl)-4-(3,4-methylenedioxyphenyl)-2H-1-benzazepine-2-one (0.35 g, 1.03 mmol) in DMF (3 ml) was added to a mixture of sodium hydride (0.036 g, 1.2 mmol, 80% mineral oil dispersion) and the mixture stirred 1 h at ambient temperature. Methyl iodide (0.4 ml, 0.91 g, 6.43 mmol) in DMF (0.5 ml) was added and the mixture stirred 48 h at ambient temperature. The reaction was quenched in water (50 ml) and extracted with ethyl acetate (3×10 ml). The combined extracts were dried (MgSO4), filtered and the solvent removed at reduced pressure to give 0.40 g of crude product. Chromatography on silica gel with 30:70 ethyl acetate-hexane gave 0.335 g of the title compound as a viscous oil. The oil was treated with hexane and the resulting white solid collected and dried to give 0.226 g (62%) of the title compound; mp 125°-127°.

Workup

  1. stirringthe mixture stirred 48 h at ambient temperature
  2. customThe reaction was quenched in water (50 ml)
  3. extractionextracted with ethyl acetate (3×10 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed at reduced pressure
  7. customto give 0.40 g of crude product

Sources & evidence

ORD record
ord-ae466539170c43d68fbf239720f30b59
Source dataset
uspto-grants-1998_10
Patent number
US05817653

Reaction notes

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