Sodium Carbonate → 6-(4-chloro-phenyl)-2,3,4,6-tetrahydro-pyrimido[2,1-a]isoindol-6-ol

HRID 1580981Notes

Reaction equation

HRID 1580981 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]2)=[C:7]1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-:23].[Na+].[Na+]>O>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:7]2([OH:23])[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3=[N:2][CH2:3][CH2:4][CH2:5][N:6]23)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 131710012HCID 131710012, compound

Product 1

HCID 122045766-(4-chloro-phenyl)-2,3,4,6-tetrahydro-pyrimido[2,1-a]isoindol-6-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 2-(3-aminopropyl)-1-(4-chlorophenyl)isoindole, hydrochloride (2 gms.) is dissolved in water and neutralized with a sodium carbonate solution. The regenerated base is extracted with ethyl acetate, dried over magnesium sulfate and evaporated to dryness. The residue is dissolved in 250 ml. of ethanol and air is bubbled through the solution for 48 hours. The precipitated white crystalline solid is separated by filtration and upon recrystallization from dimethylformamide there is obtained 6-(4-chlorophenyl)-2,3,4,6-tetrahydropyrimido[2,1-a]isoindol-6-ol, m.p. 274°-6°C. dec., which is insoluble in water and soluble in dimethylacetamide.

Workup

  1. extractionThe regenerated base is extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. customevaporated to dryness
  4. dissolutionThe residue is dissolved in 250 ml
  5. customof ethanol and air is bubbled through the solution for 48 hours
  6. customThe precipitated white crystalline solid is separated by filtration and upon recrystallization from dimethylformamide

Sources & evidence

ORD record
ord-a35b5b2c42874e318975bbb84681bbc2
Source dataset
uspto-grants-1976_01
Patent number
US03935218

Reaction notes

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