Methyl iodide → 9-Benzyl-10-methyl-9,10-diazatricyclo[4.2.1.12,5]decane

HRID 1986009Notes

Reaction equation

HRID 1986009 reaction equation
[CH2:1]([N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH:10]1[NH:17][CH:13]2[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]I>CN(C=O)C>[CH2:1]([N:8]1[CH:9]2[CH2:16][CH2:15][CH:14]1[CH:13]1[N:17]([CH3:18])[CH:10]2[CH2:11][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 508962899-Benzyl-9,10-diazatricyclo[4.2.1.12,5]decane

Product 1

HCID 508964159-Benzyl-10-methyl-9,10-diazatricyclo[4.2.1.12,5]decane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold (0° C.) solution of 9-benzyl-9,10-diazatricyclo[4.2.1.12,5]decane (J. Med. Chem. 2000, 43, 2115-2123) and TEA in an DMF (1-2 ml) was added MeI. The mixture was allowed to warm to rt and stirred for 2-3 h. The rxn mixture was evaporated to dryness and partitioned between ether and satd. NaHCO3 and ether layer separated, washed with brine and dried (Na2SO4). Evaporation of ether afforded 9-benzyl-10-methyl-9,10-diazatricyclo[4.2.1.12,5]decane as a light-brown oil. A stirred suspension of 9-benzyl-10-methyl-9,10-diazatricyclo[4.2.1.12,5]decane in EtOH containing conc. HCl (0.5 ml) and 10% Pd—C was hydrogenated under balloon pressure of hydrogen overnight. The suspension was filtered and filtrate was added dry toluene (10-15 ml) and evaporated to dryness to afford the 9-methyl-9,10-diazatricyclo[4.2.1.12,5]decane and isolated as bis-HCl salt.

Workup

  1. customThe rxn mixture was evaporated to dryness
  2. custompartitioned between ether
  3. customNaHCO3 and ether layer separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of ether

Sources & evidence

ORD record
ord-a1a004e288a74a898226d398b837a863
Source dataset
uspto-grants-2009_06
Patent number
US07547690B2

Reaction notes

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