HCID 21242088, compound → HCID 21242091, compound

HRID 1761711Notes

Reaction equation

HRID 1761711 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:35]=[CH:34][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:19]4([CH:32]=[CH:31][C:30](=[O:33])[CH:29]=[CH:28]4)[N:18]=3)[CH2:13][CH2:12]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2]>ClC1C=CC(Cl)=CC=1Cl.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]4[CH:32]=[CH:31][C:30](=[O:33])[CH:29]=[CH:28][C:19]4=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:21]=3)[CH2:13][CH2:12]2)=[CH:34][CH:35]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 21242088HCID 21242088, compound

Product 1

HCID 21242091HCID 21242091, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 131,2,4-TrichlorobenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[4-(4-ethoxycarbonylbenzyl)-1-piperazinyl]-4-phenyl-1-azaspiro[4.5]deca-1,3,6,9-tetraen-8-one (12.4 g) in 1,2,4-trichlorobenzene (250 cc) is heated for 11 hours to 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 (250 cc) and the solution is poured into silica (400 g ) contained in a column 6 cm in diameter. Elution is first performed with methylene chloride (2 liters and the corresponding eluates are rejected. Elution is then performed with a mixture of methylene chloride and methanol (99:1 by volume) (5 liters) 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 ethanol (120 cc), 3-[4-(4-ethoxycarbonylbenzyl)-1-piperazinyl]-1-phenyl-7H-pyrrolo[1,2-a]azepin-7-one (5.7 g), m.p. 129° 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 (400 g )
  4. washElution
  5. washElution
  6. additionis then performed with a mixture of methylene chloride and methanol (99:1 by volume) (5 liters)
  7. customthe corresponding eluate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  8. customAfter recrystallization of the residue in ethanol (120 cc)

Sources & evidence

ORD record
ord-1ca93a0311dc4ff889ae398dbcd716d2
Source dataset
uspto-grants-1989_05
Patent number
US04826974

Reaction notes

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