Water → HCID 67684836, compound

HRID 342232Notes

Reaction equation

HRID 342232 reaction equation
[CH2:1]([N:4]([CH3:30])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=2)(O)[CH:19]=[CH2:20])=[C:14]([NH2:29])[CH:13]=1)[CH:2]=[CH2:3].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.O.[OH-].[Na+]>C(Cl)Cl>[CH2:1]([N:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:15]([C:18]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)=[CH:19][CH:20]=[N:29]2)=[CH:16][CH:17]=1)[CH3:30])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 18434306HCID 18434306, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 67684836HCID 67684836, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.5 g of (RS)-1-[4-[6-(allyl-methyl-amino)-hexyloxy]-2-amino-phenyl]-1-(4-bromo-phenyl)-prop-2-en-1-ol is added dropwise at 0° C. within 10 min. to a suspension of 0.25 g of pyridinium chlorochromate in methylene chloride. After 1.5 hr. at room temperature water is added, the mixture is adjusted to pH 12 with 2M sodium hydroxide and extracted with methylene chloride. The organic phase is dried, concentrated and the residue is purified over silica gel with methylene chloride/methanol 95:5 as the eluent. 80 mg of the title compound are obtained. 53 mg thereof are dissolved in methylene chloride/ethyl acetate and stirred with 26 mg of fumaric acid. After filtration there is obtained allyl-[6-[4-(4-bromo-phenyl)-quinolin-7-yloxy]-hexyl]-methyl-amine.fumarate (1:3), m.p 70° C., MS: m/e 453 (M+H+, 1 Br).

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic phase is dried
  3. concentrationconcentrated
  4. customthe residue is purified over silica gel with methylene chloride/methanol 95:5 as the eluent

Sources & evidence

ORD record
ord-8dccbb2b2c8e4381817ee1b4236e3d35
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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