Water → HCID 15116194, compound

HRID 703788Notes

Reaction equation

HRID 703788 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][C:7]([NH:9][C:10]1[C:11]2[C:16]([N:17]=[C:18]3[C:23]=1[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8].O>CN(C)C=O>[N:1]([CH2:6][C:7]([NH:9][C:10]1[C:11]2[C:16]([N:17]=[C:18]3[C:23]=1[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 144713012-Chloro-N-(1,2,3,4-tetrahydroacridin-9-yl)acetamide

Product 1

HCID 15116194HCID 15116194, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 40 ml of dimethylformamide was suspended 2.84 g of sodium azide, and 10 g of 9-chloroacetylamino-1,2,3,4-tetrahydroacridine was added thereto and the mixture was reacted at room temperature for 2 hours. After addition of 32 ml of water to the mixture, precipitated crystals were filtered to give 9.7 g of 9-azidoacetylamino-1,2,3,4-tetrahydroacridine. Melting point: 190° C. (decomposed). These crystals were suspended in 500 ml of methanol, and hydrogenolysis was carried out by adding 0.5 g of palladium black at room temperature for one hour. After removal of the catalyst by filtration, the filtrate was condensed and recrystallized from methanol - isopropanol, and then filtered to give 7.4 g of the title compound. Melting point: 225° to 230° C.

Workup

  1. additionwas added
  2. customthe mixture was reacted at room temperature for 2 hours
  3. customprecipitated crystals
  4. filtrationwere filtered

Sources & evidence

ORD record
ord-9f0da72c186b4e70a0ea8d0bbccc37fe
Source dataset
uspto-grants-1991_01
Patent number
US04985430

Reaction notes

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