Piperidine → 2-Benzyloxy-5-bromo-7-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 566976Notes

Reaction equation

HRID 566976 reaction equation
N1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([O:14][N:15]1[C:24](=[O:25])[C:23]2[CH:26]=[C:27]([Br:32])[C:28]([N+:29]([O-])=O)=[C:21]3[C:22]=2[C:17](=[CH:18][CH:19]=[CH:20]3)[C:16]1=[O:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:34]([O:41][N:42]1[C:51](=[O:52])[C:50]2[CH:53]=[C:54]([Br:56])[CH:55]=[C:48]3[C:49]=2[C:44](=[CH:45][CH:46]=[C:47]3[N+:57]([O-])=O)[C:43]1=[O:60])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C=O)C>[CH2:7]([O:14][N:15]1[C:24](=[O:25])[C:23]2[CH:26]=[C:27]([Br:32])[C:28]([N:29]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:21]3[C:22]=2[C:17](=[CH:18][CH:19]=[CH:20]3)[C:16]1=[O:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:34]([O:41][N:42]1[C:51](=[O:52])[C:50]2[CH:53]=[C:54]([Br:56])[CH:55]=[C:48]3[C:49]=2[C:44](=[CH:45][CH:46]=[C:47]3[N:57]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:43]1=[O:60])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 226239822-Benzyloxy-5-bromo-6-nitro-benzo[de]isoquinoline-1,3-dioneHCID 226239882-Benzyloxy-5-bromo-7-nitro-benzo[de]isoquinoline-1,3-dione

Product 2

HCID 226238972-Benzyloxy-5-bromo-7-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneHCID 226239132-Benzyloxy-5-bromo-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of piperidine (0.40 g, 4.7 mmol) in 5 mL of DMF was added a mixture of 2-benzyloxy-5-bromo-6-nitro-benzo[de]isoquinoline-1,3-dione (A) and 2-benzyloxy-5-bromo-7-nitro-benzo[de]isoquinoline-1,3-dione (B) (0.50 g, 1.2 mmol, from Example S1-A,B). The reaction was heated to 120° C. for 4 hours, cooled, and the solvent removed under vacuum. The residue was chromatographed using chloroform/ethyl acetate (10:1) to give a mixture of the title compounds which were separated by crystallization from chloroform/hexane/ethyl acetate (5:5:1) to give 0.27 g of 2-benzyloxy-5-bromo-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (A) and 0.10 g of 2-benzyloxy-5-bromo-7-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (B).

Workup

  1. temperaturecooled
  2. customthe solvent removed under vacuum
  3. customThe residue was chromatographed
  4. customto give
  5. customwere separated by crystallization from chloroform/hexane/ethyl acetate (5:5:1)

Sources & evidence

ORD record
ord-edd21445b5984e7894f5bb3b3c6b14a0
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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