Formic Acid → 2-[(6,11-Dihydro-5H-dibenzo[b,e]azepin-6-yl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 1033849Notes

Reaction equation

HRID 1033849 reaction equation
[C:1]1(=[O:27])[N:5]([CH2:6][C:7]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[CH:10]=[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=23)[C:4](=[O:22])[C:3]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:2]12.C(O)=O.[H][H]>CN(C)C=O.[Pd]>[C:4]1(=[O:22])[N:5]([CH2:6][CH:7]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[CH2:10][C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]2=3)[C:1](=[O:27])[C:2]2=[CH:26][CH:25]=[CH:24][CH:23]=[C:3]12

Participants

6

Reactant 3

HCID 284Formic AcidHCID 190249922-(5H-Dibenz[b,e]azepin-6-ylmethyl)-1H-isoindole-1,3(2H)-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 99466272-[(6,11-Dihydro-5H-dibenzo[b,e]azepin-6-yl)methyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of 110.0 kg of 6-phthalimidomethyl-5H-dibenz[b,e]azepine in 911.4 liters of dimethylformamide, 28.7 kg of formic acid and a suspension of 12.5 kg of 10% palladium charcoal in 25 liters of dimethylformamide is fed into a 1200 liter VA-propulsive jet loop reactor. The reaction mixture is heated to 70° C. and hydrogenated under 7 bar of absolute hydrogen pressure. After the catalyst has been filtered off and the reaction equipment and catalyst have been washed with 80 liters of dimethylformamide, 960 liters of dimethylformamide are distilled off from the combined filtrates at 70° to 80° C. After cooling to 50° C., 150 liters of acetone are added, then after further cooling to 15° C. the precipitated crystals are centrifuged off, washed with acetone and dried.

Workup

  1. customis fed into a 1200 liter VA-propulsive jet loop reactor
  2. filtrationAfter the catalyst has been filtered off
  3. washthe reaction equipment and catalyst have been washed with 80 liters of dimethylformamide, 960 liters of dimethylformamide
  4. distillationare distilled off from the combined filtrates at 70° to 80° C
  5. addition150 liters of acetone are added
  6. temperatureafter further cooling to 15° C. the precipitated crystals
  7. washwashed with acetone
  8. customdried

Sources & evidence

ORD record
ord-7e6b63768c31432f833c6295e0411a32
Source dataset
uspto-grants-1994_05
Patent number
US05312916

Reaction notes

Loading…