Acetone → HCID 67684555, compound

HRID 342228Notes

Reaction equation

HRID 342228 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:17][CH:18]=[CH2:19])[CH3:16])[CH:5]=[CH:4][C:3]=1[C:20]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)=O.OS(O)(=O)=O.[CH3:34][C:35]([CH3:37])=O.[OH-].[NH4+]>C(O)(=O)C.O>[CH2:17]([N:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:6]1[CH:7]=[C:2]2[C:3]([C:20]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)=[CH:34][C:35]([CH3:37])=[N:1]2)=[CH:4][CH:5]=1)[CH3:16])[CH:18]=[CH2:19]

Participants

7

Reactant 4

HCID 180Acetone2×HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 10873957HCID 10873957, compound

Product 1

HCID 67684555HCID 67684555, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 360 mg of [2-amino-4-[6-(allyl-methyl-amino)-hexyloxy]-phenyl]-(4-bromo-phenyl)-methanone in 1.6 ml of acetic acid is treated with 0.01 ml of H2SO4 and 0.4 ml of acetone and boiled at 95° C. for 21 hrs., with a further 0.4 ml of acetone being added after 6 hrs. At 0° C. the reaction is poured into an ice-cold solution of 1.2 ml of 25% ammonium hydroxide solution in 3.5 ml of water and the mixture is subsequently extracted with methylene chloride. After drying the organic phase is evaporated and the residue is purified over silica gel with methylene chloride/methanol (95:5). The title compound obtained (200 mg) is crystallized with 24.6 mg of fumaric acid from methylene chloride/methanol/ether. There are obtained 56 mg of allyl-[6-[4-(4-bromo-phenyl)-2-methyl-quinolin-7-yloxy]-hexyl]-methyl-amine.fumarate (1:2), m.p. 88°-93° C., MS: m/e 467 (M+H+, 1 Br).

Workup

  1. extractionthe mixture is subsequently extracted with methylene chloride
  2. customAfter drying the organic phase
  3. customis evaporated
  4. customthe residue is purified over silica gel with methylene chloride/methanol (95:5)

Sources & evidence

ORD record
ord-ee817bb6ddf44ce789c66c330d69274f
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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