HCID 67759048, compound → HCID 15231840, compound

HRID 1779703Notes

Reaction equation

HRID 1779703 reaction equation
C1(C[N:8](CC2C=CC=CC=2)[C:9]2[C:18]3[N:19]=[CH:20][N:21]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:17]=3[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=2)C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)=O>[C:23]1([CH2:22][N:21]2[C:17]3[C:16]4[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=4[N:10]=[C:9]([NH2:8])[C:18]=3[N:19]=[CH:20]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 67759048HCID 67759048, compound

Product 1

HCID 15231840HCID 15231840, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 284Formic AcidSolvent2×

Procedure

N,N,1-Tris(phenylmethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine (4.49 g, 9.8 mmole), palladium hydroxide on carbon (1.0 g, Pearlman's catalyst) and formic acid (20 mL) were combined and heated at reflux for 4 days. During the course of the reaction the formic acid evaporated out of the reaction vessel. The residue was diluted with formic acid (15 mL) and water (20 mL) then filtered through a layer of celite. The filtrate was basified with 28% ammonium hydroxide then extracted with methylene chloride (3×100 mL). The methylene chloride extracts were combined, dried over magnesium sulfate and concentrated to provide 2.5 g of a yellow foam. The foam was loaded onto a 3 cm by 15 cm column of silica gel and eluted with methylene chloride:methanol 90:10. The early fractions were combined and evaporated to provide 0.54 g of N,2-bis(phenylmethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid, m.p. 199°-200° C. The later fractions were combined and evaporated to provide 1.58 g of a mixture of 6,7,8,9-tetrahydro-N-phenylmethyl-1H-imidazo[4,5-c]quinolin-4-amine and 6,7,8,9-tetrahydro-1-phenylmethyl-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid. This mixture was loaded onto a 3 cm by 20 cm column of silica gel and eluted with methylene chloride:methanol 90:10. 80 fractions, 6 mL each, were collected. Fractions 18-27 were combined and evaporated to provide 0.48 g of 6,7,8,9-tetrahydro-N-phenylmethyl-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, m.p. 168°-170° C. Fractions 40-57 were combined and evaporated to provide 180 mg of the desired product, 6,7,8,9-tetrahydro-1-phenylmethyl-1H-imidazo[4,5-c]quinolin-4-amine, as a white solid, m.p. 231°-233° C. (dec). Analysis: Calculated for: C18H19N4 +1/5 CH2Cl2 : %C, 69.95; %H, 6.28; %N, 18.97; Found: %C, 70.44; %H, 6.16; %N, 18.93.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 days
  3. customevaporated out of the reaction vessel
  4. additionThe residue was diluted with formic acid (15 mL) and water (20 mL)
  5. filtrationthen filtered through a layer of celite
  6. extractionthen extracted with methylene chloride (3×100 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ef9052dcbca74e8fba1956c8ef287701
Source dataset
uspto-grants-1997_05
Patent number
US05627281

Reaction notes

Loading…