Potassium Hydroxide → HCID 11223585, compound

HRID 1821092Notes

Reaction equation

HRID 1821092 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:15](=[CH:16][CH:17]=1)[C:14]([NH2:18])=[C:13]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12]1)=[N:7]2.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br>CS(C)=O>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:18][C:14]1[C:15]2[C:6]([N:7]=[C:8]3[C:13]=1[CH2:12][CH2:11][CH2:10][CH2:9]3)=[CH:5][C:4]([Cl:3])=[CH:17][CH:16]=2

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 783091,7-DibromoheptaneHCID 103990689-AMINO-6-CHLORO-1,2,3,4-TETRAHYDRO-ACRIDINE

Product 1

HCID 11223585HCID 11223585, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium hydroxide (95 mg, 1.7 mmoL) was added to a solution of 6-chloro-1,2,3,4-tetrahydro-acridin-9-ylamine (395 mg, 1.7 mmoL) in dimethylsulfoxide (15 ml) and the mixture was stirred vigorously under nitrogen at room temperature for 2 h. 1,7-Dibromoheptane (438 mg, 1.7 mmoL) was added, and the reaction was continued to stir at room temperature for 12 h. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The combined ethyl acetate extract was dried, filtered and concentrated. The resulting residue was purified by column chromatography on silica gel using hexane/ethyl acetate/triethyl amine (8/2/1) to provide the desired product (244 mg, 0.60 mmoL) in 35% yield.

Workup

  1. stirringto stir at room temperature for 12 h
  2. extractionextracted with ethyl acetate
  3. extractionThe combined ethyl acetate extract
  4. customwas dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7fc91e80b31146e8814f7593282966bb
Source dataset
uspto-grants-2009_10
Patent number
US07605265B2

Reaction notes

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