Sodium Hydroxide → HCID 18668744, compound

HRID 1058624Notes

Reaction equation

O([C:8]1[C:17]2[N:18]=[CH:19][N:20]([CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1)C1C=CC=CC=1.C([O-])(=O)C.[NH4+:40].[OH-].[Na+]>O>[NH2:40][C:8]1[C:17]2[N:18]=[CH:19][N:20]([CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:25][CH2:24]3)[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 4.40 g of tert-butyl 4-[2-(4-phenoxy-1H-imidazo[4,5-c]-quinolin-1-yl)ethyl]-1-piperidinecarboxylate and 34.5 g of ammonium acetate was stirred at 140° C. for 3 hours. The reaction mixture was added with water, adjusted to pH 9 with 10% aqueous sodium hydroxide solution, and extracted with methylene chloride. The extract was washed with saturated brine, and dried, and then the solvent was evaporated. The resulting residue was purified by alumina column chromatography using methylene chloride—methanol (100:1 to 20:1) as eluting solvents, and washed with diisopropyl ether to give 1.88 g of colorless crystals. Recrystallization from ethyl acetate gave colorless crystals having the melting point of from 193 to 193.5° C.

Workup

extractionextracted with methylene chloride
washThe extract was washed with saturated brine
customdried
customthe solvent was evaporated
customThe resulting residue was purified by alumina column chromatography
washas eluting solvents
washwashed with diisopropyl ether

Sources & evidence

ORD record: ord-1000bc96acc84b4ba3b3e3ed836bdeec
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518265B1

Reaction notes

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