Methyl iodide → HCID 19347381, compound

HRID 1638189Notes

Reaction equation

HRID 1638189 reaction equation
[ClH:1].[CH2:2]1[CH:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:5][CH2:4][CH:3]1[N:12]1[CH2:28][CH2:27][C:15]2([N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][NH:17][C:16]2=[O:26])[CH2:14][CH2:13]1.[H-].[Na+].[CH3:31]I>CN(C=O)C>[ClH:1].[CH2:2]1[CH:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[CH2:5][CH2:4][CH:3]1[N:12]1[CH2:28][CH2:27][C:15]2([N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][N:17]([CH3:31])[C:16]2=[O:26])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19347380HCID 19347380, compound

Product 1

HCID 19347381HCID 19347381, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

8-(Decahydro-naphthalen-2-yl)-1-phenyl-1,3,8-triaza-spiro[4,5]decan-4-one hydrochloride (1:1) (1.2 mmol) was suspended in DMF (20 ml). Sodium hydride (2.4 mmol) was added and the mixture was stirred at 80° C. for 1 h. The mixture was cooled to room temperature, methyl iodide (1.2 mmol) was added and the mixture was stirred for 18 h. DMF was evaporated, sodium bicarbonate and ethylacetate were added. The organic phase was washed with brine, dried with MgSO4 and concentrated. Chromatography on silica gel (methylenchloride/methanol, 98:2) yielded the desired product which was crystallized as its HCl-salt from ethylacetate/ethanol. 0.19 g (36%) 8-(decahydro-naphthalen-2-yl)-3-methyl-1-phenyl-1,3,8-triaza-spiro[4,5]decan-4-one hydrochloride (1:1) as a colorless solid, m.p.>250° C. and MS: m/e=382 (M+H+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringthe mixture was stirred for 18 h
  3. customDMF was evaporated
  4. additionsodium bicarbonate and ethylacetate were added
  5. washThe organic phase was washed with brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2ba9806b7fe44049b62b6bd8d4d3d375
Source dataset
uspto-grants-2000_03
Patent number
US06043366

Reaction notes

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