1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Benzyloxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 278999Notes

Reaction equation

HRID 278999 reaction equation
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[CH:21][C:22](Br)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]1[CH2:35][CH2:34][N:33]2C(=NC[CH2:31][CH2:32]2)CC1>N1CCCCC1>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[CH:21][C:22]([N:33]3[CH2:32][CH2:31][CH2:25][CH2:35][CH2:34]3)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

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

Product 1

HCID 226240632-Benzyloxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

2-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione (0.8 g, 2.1 mmol, from Example M) was reacted in piperidine (3.0 mL) in the presence of DBU (0.05 mL) following the procedure of Example 18 to give 0.8 g of 2-benzyloxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione. Hydrogenation of 2-benzyloxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.4 g, 1.0 mmol) in the presence of 10% Pd/C (0.2 g) in DMA (30 mL) afforded 0.28 g of the title compound, mp 222-224° C.;

Sources & evidence

ORD record
ord-d3201f4748654f1eaeae47c0a2b36baf
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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