Dimethylformamide → HCID 18668741, compound

HRID 1058632Notes

Reaction equation

HRID 1058632 reaction equation
F[C:2](F)(F)[C:3](O)=O.[Cl:8][C:9]1[C:18]2[N:19]=[CH:20][N:21]([CH2:22][CH2:23][CH:24]3[CH2:29]CNC[CH2:25]3)[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1.[C:30](=O)([O-])[O-].[K+].[K+].[OH-].[Na+].[CH3:38][N:39]([CH3:42])[CH:40]=O>C(Br)CCC>[ClH:8].[CH2:38]([N:39]1[CH2:42][CH2:25][CH:24]([CH2:23][CH2:22][N:21]2[C:17]3[C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=[C:9]([Cl:8])[C:18]=3[N:19]=[CH:20]2)[CH2:29][CH2:40]1)[CH2:30][CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 18668816HCID 18668816, compound

Product 1

HCID 18668741HCID 18668741, compound

Reagents, catalysts & solvents 1

HCID 8002Butyl bromideSolvent

Procedure

To a suspension of 1.20 g of 4-chloro-1-[2-(4-piperidyl)ethyl]-1H-imidazo-[4,5-c]quinoline trifluoroacetate and 0.77 g of potassium carbonate in 6 ml of N,N-dimethylformamide, 0.30 ml of n-butyl bromide was added dropwise at room temperature, and the mixture was stirred for 5 hours. The reaction mixture was adjusted to pH 10 with 10% aqueous sodium hydroxide solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried, and then the solvent was evaporated to give 0.92 g of a pale brown liquid. The resulting liquid was dissolved in tetrahydrofuran. The solution was filtered on silica gel, and the filtrate was concentrated to give 0.87 g of a colorless solid. Hydrochloride was prepared in a conventional method. Recrystallization from a mixture of methanol and ethyl acetate gave colorless crystals having the melting point of from 144 to 158° C.

Workup

  1. additionwas added dropwise at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively with water and saturated brine
  4. customdried
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c458e9979a01453bb72b16b2fd663940
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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