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

HRID 1986010Notes

Reaction equation

HRID 1986010 reaction equation
[CH2:1]([N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH:10]1[N:17](C)[CH:13]2[CH2:12][CH2:11]1)C1C=CC=CC=1.[H][H]>CCO.[Pd]>[CH3:1][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

Participants

5

Reactant 2

HCID 508964159-Benzyl-10-methyl-9,10-diazatricyclo[4.2.1.12,5]decaneHCID 178418361HCID 178418361, compound

Product 1

HCID 508964139-Methyl-9,10-diazatricyclo[4.2.1.12,5]decane

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23938PalladiumSolvent

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. filtrationThe suspension was filtered
  2. additionfiltrate was added dry toluene (10-15 ml)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-e0fb0253a33941d8b60d205b7a274b3e
Source dataset
uspto-grants-2009_06
Patent number
US07547690B2

Reaction notes

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