Hydrogen Bromide → HCID 135789544, compound

HRID 1761706Notes

Reaction equation

HRID 1761706 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)[C:16]3([CH:31]=[CH:30][C:29](=[O:32])[CH:28]=[CH:27]3)[N:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br>C(O)(=O)C.C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)[C:16]3([CH:31]=[CH:30][C:29](=[O:32])[CH:28]=[CH:27]3)[N:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 13691025HCID 13691025, compound

Product 1

HCID 135789544HCID 135789544, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

2-(4-Benzyl-1-piperazinyl)-4-(4-hydroxyphenyl)-1-azaspiro[4.5]deca-1,3,6,9-tetraen-8-one can be obtained in the following manner: 2-(4-benzyl-1-piperazinyl)-4-(4-methoxyphenyl)-1-azaspiro[4.5]deca-1,3,6,9-tetraen-8-one (6.3 g) dissolved in acetic acid (150 cc) and a 48% strength solution of hydrobromic acid (100 cc) are heated for 12 hours to a temperature of about 100° C. After being cooled to a temperature of about 20° C., the solution is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. Crushed ice (200 g) is added to the residue, followed by 11N aqueous ammonia solution (500 cc). The aqueous solution is washed with chloroform (2×300 cc). The organic fractions are combined, washed with distilled water (200 cc), dried over anhydrous sodium sulphate, filtered and evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue obtained is dissolved in chloroform (200 cc) and the solution is poured into silica (120 g) contained in a column 3.2 cm in diameter. Elution is performed first with chloroform (1 liter) and the corresponding eluate is rejected. Elution is then performed with a mixture of chloroform and methanol (95:5 by volume) (1 liter) and the corresponding eluate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. 2-(4-Benzyl-1-piperazinyl)-4-(4-hydroxyphenyl)-1-azaspiro[4.5]deca-1,3,6,9-tetraen-8-one (3.8 g) is thereby obtained in the form of a brown cake.

Workup

  1. customthe solution is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  2. additionCrushed ice (200 g) is added to the residue
  3. washThe aqueous solution is washed with chloroform (2×300 cc)
  4. washwashed with distilled water (200 cc)
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  8. customThe residue obtained
  9. additionthe solution is poured into silica (120 g)
  10. washElution
  11. washElution
  12. additionis then performed with a mixture of chloroform and methanol (95:5 by volume) (1 liter)
  13. customthe corresponding eluate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C

Sources & evidence

ORD record
ord-7f1a66f601e444db9023b29b3ef30c34
Source dataset
uspto-grants-1989_05
Patent number
US04826974

Reaction notes

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