Morpholine → 2-Benzyloxy-6-(morpholin-4-yl)-benzo[de]isoquinoline-1,3-dione

HRID 278998Notes

Reaction equation

HRID 278998 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.C1CCN2C(=NCCC2)CC1.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[CH:21][C:22]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]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 3

HCID 8083MorpholineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 226240382-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione

Product 1

HCID 226239062-Benzyloxy-6-(morpholin-4-yl)-benzo[de]isoquinoline-1,3-dione

Procedure

2-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione (0.8 g, 2.1 mmol, from Example M) was reacted in morpholine (3.0 mL) in the presence of DBU (0.05 mL) following the procedure of Example 18 to give 0.6 g of 2-benzyloxy-6-(morpholin-4-yl)-benzo[de]isoquinoline-1,3-dione. Hydrogenation of 2-benzyloxy-6-(morpholin-4-yl)-benzo[de]isoquinoline-1,3-dione (0.4 g, 0.9 mmol) in the presence of 10% Pd/C (0.2 g) in DMA (30 mL) afforded 0.2 g of the title compound, mp 235-237° C.;

Sources & evidence

ORD record
ord-ee3f08a5dbaa47768056acb5ec7b9bd3
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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