HCID 21108201, compound → HCID 9824039, compound

HRID 1766020Notes

Reaction equation

HRID 1766020 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:16]3[C:25]4[C:20](=[CH:21][C:22]([CH:26](O)[CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])=[CH:23][CH:24]=4)[CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>S(=O)(=O)(O)O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([N:16]3[C:25]4[C:20](=[CH:21][C:22](/[CH:26]=[CH:27]/[CH2:28][N:29]([CH3:31])[CH3:30])=[CH:23][CH:24]=4)[CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 21108201HCID 21108201, compound

Product 1

HCID 9824039HCID 9824039, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
52.5 °C

Procedure

Concd. sulfuric acid (4 drops) was added to a solution of 3-[1-[(4′-chloro[1,1-biphenyl]-4-yl)carbonyl]-1,2,3,4-tetrahydro-6-quinolinyl]-3-hydroxy-N,N-dimethyl-1-propanamine (0.1 g) obtained in Example 4 in acetic acid (1 mL), and the mixture was stirred at 50 to 55° C. for 3 hours. After the solvent was distilled away under reduced pressure, the residues were made basic with 2 N aqueous sodium hydroxide and then extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The resultant residues were purified by alumina column chromatography (developing solvent; ethyl acetate) and crystallized from diethyl ether, whereby the title compound (75 mg) was obtained as colorless powder with a mp of 162 to 164° C.

Workup

  1. distillationAfter the solvent was distilled away under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe resultant residues were purified by alumina column chromatography (developing solvent; ethyl acetate)
  7. customcrystallized from diethyl ether, whereby the title compound (75 mg)
  8. customwas obtained as colorless powder with a mp of 162 to 164° C.

Sources & evidence

ORD record
ord-7ed56da99d93425eb931bd5d0ff83a14
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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