Methyl iodide → (3aR*,10aS*)-9-Benzyl-4-methyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 356159Notes

Reaction equation

HRID 356159 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[NH:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CI.[C:27](=O)([O-])O.[Na+]>CN(C)C=O.O>[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[N:11]([CH3:27])[C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 70109795(3aR*,10aS*)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta [e][1,4]diazepin-10(1H)-one

Product 1

HCID 70109997(3aR*,10aS*)-9-Benzyl-4-methyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (3aR*,10aS*)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-one (2.93 g, 10 mmol) in N,N-dimethylformamide (20 mL) were added sodium hydride (60% liquid paraffin dispersion, 0.41 g, 10 mmol) and methyl iodide (1.3 mL, 21 mmol). The mixture was stirred for 13 hours at 80° C. To the reaction mixture were added water and, then, a saturated aqueous solution of sodium hydrogencarbonate. The mixture was subjected extraction with ethyl acetate three times. Organic layers were combined and washed with water and, then, with a saturated aqueous solution of sodium hydrogencarbonate, which was dried over sodium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was purified by silica-gel column chromatography (hexane-ethyl acetate 10:1) to give 2.52 g (yield 82%) of the titled compound. The sample for analytical experiment was prepared by recrystallization from methanol. m.p. 123°-125° C.

Workup

  1. extractionextraction with ethyl acetate three times
  2. washwashed with water
  3. dry with materialwith a saturated aqueous solution of sodium hydrogencarbonate, which was dried over sodium sulfate
  4. filtrationfollowed by filtration and concentration under reduced pressure
  5. customThe concentrate was purified by silica-gel column chromatography (hexane-ethyl acetate 10:1)

Sources & evidence

ORD record
ord-eb4d42376fe34b1185939068b0ba6a30
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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