Phenol → tert-Butyl 4-[2-(4-phenoxy-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-1-piperidinecarboxylate

HRID 1058623Notes

Reaction equation

HRID 1058623 reaction equation
Cl[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:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[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:30]1([OH:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[OH-].[K+].[OH-].[Na+]>>[O:36]([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:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[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:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 4

HCID 996PhenolHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 18668812tert-butyl 4-[2-(4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-1-piperidinecarboxylate

Product 1

HCID 18668801tert-Butyl 4-[2-(4-phenoxy-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-1-piperidinecarboxylateYield 70.7%

Conditions

Temperature
120 °C

Procedure

A mixture of 4.46 g of tert-butyl 4-[2-(4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-1-piperidinecarboxylate, 10.1 g of phenol and 1.80 g of potassium hydroxide was stirred at 120° C. for 7 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 10% aqueous sodium hydroxide solution and saturated brine, and dried, and then the solvent was evaporated to give a brown liquid. The resulting brown liquid was purified by silica gel column chromatography using ethyl acetate as an eluting solvent to give 3.59 g of a colorless solid. Recrystallization from a mixture of ethyl acetate and n-hexane gave colorless crystals having the melting point of from 130.5 to 132.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with 10% aqueous sodium hydroxide solution and saturated brine
  3. customdried
  4. customthe solvent was evaporated
  5. customto give a brown liquid
  6. customThe resulting brown liquid was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9445107bd7794df5b5e8c23e6d8af2ba
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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