N-3-Bromopropylphthalimide → HCID 20081633, compound

HRID 1609462Notes

Reaction equation

HRID 1609462 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12].[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32]>CN(C)C=O>[O:12]=[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][N:6]1[CH2:5][C:4]1[CH:3]=[C:2]([CH:15]=[CH:14][CH:13]=1)[O:1][CH2:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32]

Participants

5

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 20081637HCID 20081637, compound

Product 1

HCID 20081633HCID 20081633, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
65 °C

Procedure

In an argon stream with ice cooling, a solution of 2.3 g of the 1-(3-hydroxybenzyl)-2-piperidone obtained in Reference Example 2 in 10 ml of N,N-dimethylformamide was added dropwise to a soltuion of 0.44 g of 60% sodium hydride in 5 ml of N,N-dimethylformamide. Subsequently, a solution of 2.8 g of N-(3-bromopropyl)phthalimide in 10 ml of N,N-dimethylformamide was added dropwise to the mixture at room temperature, followed by stirring at 65° C. for 8 hours. The resulting mixture was cooled, ice-cold water was thereafter added thereto, the mixture was subjected to extraction with diethyl ether, 6N hydrochloric acid was then added to the organic layer for extraction into the aqueous layer, and the aqueous layer was made alkaline with sodium hydroxide, followed by extraction with diethyl ether again. The organic layer was dried over magnesium sulfate and thereafter distilled to remove the solvent, giving N-[3-[3-(2-oxopiperidinomethyl)-phenoxy]propyl]phthalimide. This compound was hydrolyzed with hydrazine in the same manner as in Example 1, (ii) to afford 1.4 g of 3-[3-(2-oxopiperidinomethyl)phenoxy]propylamine (yield 51% ).

Workup

  1. temperatureThe resulting mixture was cooled
  2. additionice-cold water was thereafter added
  3. extractionthe mixture was subjected to extraction with diethyl ether, 6N hydrochloric acid
  4. additionwas then added to the organic layer for extraction into the aqueous layer
  5. extractionfollowed by extraction with diethyl ether again
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. distillationdistilled
  8. customto remove the solvent

Sources & evidence

ORD record
ord-ecd4e4df63b64442bb7465d1cae4afcd
Source dataset
uspto-grants-1995_03
Patent number
US05401739

Reaction notes

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