HCID 21242077, compound → HCID 21242084, compound

HRID 1761709Notes

Reaction equation

HRID 1761709 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]2([CH:18]=[CH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[N:12]=[C:11]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)[CH2:22][CH2:21]2)[CH:10]=1>ClC1C=CC(Cl)=CC=1Cl.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]([N:20]2[CH2:21][CH2:22][N:23]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)[CH2:24][CH2:25]2)[N:12]2[CH:18]=[CH:17][C:16](=[O:19])[CH:15]=[CH:14][C:13]=12

Participants

4

Reactant 1

HCID 21242077HCID 21242077, compound

Product 1

HCID 21242084HCID 21242084, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 131,2,4-TrichlorobenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-methoxyphenyl)-2-[4-(4-methylbenzyl)-1-piperazinyl]-1-azaspiro[4.5]deca-1,3,6,9-tetraen-8-one (2.8 g) in 1,2,4-trichlorobenzene (80 cc) is heated for 4 hours at a temperature of about 210° C. After evaporation to dryness under reduced pressure (1 mm Hg; 0.13 kPa) at 40° C., the residue obtained is dissolved in methylene chloride (50 cc) and the solution is poured into silica (60 g) contained in a column 2 cm in diameter. Elution is first performed with a mixture of methylene chloride and methanol (99:1 by volume) (200 cc); the corresponding eluates are rejected. Elution is then performed with a mixture of methylene chloride and methanol (99:1 by volume) (450 cc) and the corresponding eluate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. After recrystallization of the residue in acetonitrile (75 cc), 1-(2-methoxyphenyl)-3-[4-(4-methylbenzyl)-1-piperazinyl]-7H-pyrrolo[1,2-a]azepin-7-one (1.8 g), m.p. 186° C., is obtained.

Workup

  1. customAfter evaporation to dryness under reduced pressure (1 mm Hg; 0.13 kPa) at 40° C.
  2. customthe residue obtained
  3. additionthe solution is poured into silica (60 g)
  4. washElution
  5. additionis first performed with a mixture of methylene chloride and methanol (99:1 by volume) (200 cc)
  6. washElution
  7. additionis then performed with a mixture of methylene chloride and methanol (99:1 by volume) (450 cc)
  8. customthe corresponding eluate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  9. customAfter recrystallization of the residue in acetonitrile (75 cc)

Sources & evidence

ORD record
ord-863f9df991ca44c783a59443508d6863
Source dataset
uspto-grants-1989_05
Patent number
US04826974

Reaction notes

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