Hydrochloric Acid → 4-Amino-1-[2-(4-piperidyl)ethyl]-1h-imidazo[4,5-c]quinoline hydrochloride
Reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.C(OCC)(=O)C.[ClH:36].[OH-].[Na+]>O>[ClH:36].[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1Participants
Procedure
A mixture of 1.57 g of tert-butyl 4-[2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-1-piperidinecarboxylate and 40 ml of ethyl acetate solution of hydrogen chloride was stirred at room temperature for 5 hours. The reaction mixture was added with water, adjusted to pH 10 with 10% aqueous sodium hydroxide solution, and extracted with methylene chloride. The extract was dried, and the solvent was evaporated. The resulting residue was washed with ethyl acetate to give 1.01 g of pale brown crystals. The resulting crystals were purified by alumina column chromatography using methylene chloride—methanol (40:1 to 20:1) as eluting solvents, and washed with diisopropyl ether to give colorless crystals. Hydrochloride was prepared in a conventional method. Recrystallization from ethanol gave colorless crystals having the melting point of from 243 to 244° C. (decomposition).
Workup
- extractionextracted with methylene chloride
- customThe extract was dried
- customthe solvent was evaporated
- washThe resulting residue was washed with ethyl acetate
Sources & evidence
- ORD record
- ord-a1698816b7824719b956d51eafa72079
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06518265B1
Reaction notes
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