Ethyl Acetate → HCID 13691028, compound

HRID 1761702Notes

Reaction equation

HRID 1761702 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]3([CH:25]=[CH:24][C:23](=[O:26])[CH:22]=[CH:21]3)[N:11]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].C(OCC)(=O)C>C(Cl)Cl>[CH2:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:11]3[CH:25]=[CH:24][C:23](=[O:26])[CH:22]=[CH:21][C:12]3=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)[CH2:8][CH2:9]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 8857Ethyl Acetate2×HCID 13691018HCID 13691018, compound

Product 1

HCID 13691028HCID 13691028, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
20 °C

Procedure

2-(4-Allyl-1-piperazinyl)-4-phenyl-1-azaspiro[4.5]deca-1,3,6,9-tetraen-8-one (40 g) is heated for 10 minutes to a temperature of about 220° C. After being cooled to a temperature of about 20° C., the residue is dissolved in methylene chloride (500 cc) and poured into silica (1 kg) contained in a column 6.5 cm in diameter. Successive elutions are performed with pure methylene chloride (1 liter), a mixture of methylene chloride and ethyl acetate (90:10 by volume) (1 liter) and a mixture of methylene chloride and ethyl acetate (80:20 by volume) (1 liter); the corresponding eluates are discarded. Elution is then performed with a mixture of methylene chloride and ethyl acetate (70:30 by volume) (3 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 acetonitrile (200 cc), 3-(4-allyl-1-piperazinyl)-1-phenyl-7H-pyrrolo[1,2-a]azepin-7-one (28 g), m.p. 125° C., is obtained.

Workup

  1. additionpoured into silica (1 kg)
  2. washElution
  3. additionis then performed with a mixture of methylene chloride and ethyl acetate (70:30 by volume) (3 liters)
  4. customthe corresponding eluate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  5. customAfter recrystallization of the residue in acetonitrile (200 cc)

Sources & evidence

ORD record
ord-c89c91f4cc924dfdb324adc4829e4599
Source dataset
uspto-grants-1989_05
Patent number
US04826974

Reaction notes

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