Pyrrolidine → 2-Benzyloxy-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 278997Notes

Reaction equation

HRID 278997 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]([O:13][N:14]1[C:23](=[O:24])[C:22]2[CH:25]=[CH:26][C:27](Br)=[C:20]3[C:21]=2[C:16](=[CH:17][CH:18]=[CH:19]3)[C:15]1=[O:29])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1CCN2C(=NCCC2)CC1>O>[CH2:6]([O:13][N:14]1[C:15](=[O:29])[C:16]2[CH:17]=[CH:18][C:19]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:20]3[C:21]=2[C:22](=[CH:25][CH:26]=[CH:27]3)[C:23]1=[O:24])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 226240382-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione

Product 1

HCID 226239982-Benzyloxy-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyrrolidine (3 mL) was added to 2-benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione (0.8 g, 2.1 mmol, from Example M) in the presence of DBU (0.05 mL). The mixture was refluxed for 2 hours and poured into water (50 mL). The precipitate formed was filtered and dried to give 0.8 g of 2-benzyloxy-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione. The hydrogenation of 2-benzyloxy-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.4 g, 1.1 mmol) in the presence of 10% Pd/C (0.2 g) in DMA (30 mL) gave 0.27 g of the title compound, mp 268-270° C.;

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-9b477e69511e4c228623e1033e7c1768
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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