Allyl bromide → HCID 19769373, compound

HRID 1590049Notes

Reaction equation

HRID 1590049 reaction equation
Cl.[NH2:2][C:3]1[C:4]([Cl:24])=[CH:5][C:6]2[C:7](=[O:23])[N:8]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:9](=[O:16])[C:10]3[C:15]=2[C:14]=1[CH:13]=[CH:12][CH:11]=3.C(N(CC)CC)C.[CH2:32](Br)[CH:33]=[CH2:34]>CN(C)C=O>[NH2:2][C:3]1[C:4]([Cl:24])=[CH:5][C:6]2[C:7](=[O:23])[N:8]([CH:17]3[CH2:18][CH2:19][N:20]([CH2:34][CH:33]=[CH2:32])[CH2:21][CH2:22]3)[C:9](=[O:16])[C:10]3[C:15]=2[C:14]=1[CH:13]=[CH:12][CH:11]=3

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 19769421HCID 19769421, compound

Product 1

HCID 19769373HCID 19769373, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 6-amino-5-chloro-2,3-dihydro-2-(piperidin-4-yl)-1H-benz[de]isoquinoline-1,3-dione hydrochloride (0.5 g; 1.37 mmol), prepared as in Example 10, and triethylamine (0.3 g; 3.0 mmol) in N,N-dimethylformamide (10 mL), was added allyl bromide (0.17 g; 1.4 mmol) in N,N-dimethylformamide (approximately 2 mL). The reaction mixture was stirred for 1.5 hours and the solvent removed. The residue was stirred with ammonium hydroxide and methylene chloride (50 mL). The aqueous layer was further extracted with methylene chloride (2×50 mL) and purification of the combined methylene chloride layers by column chromatography (silica gel; 3% methanol in CH2Cl2 and approximately 1% NH4OH) gave 6-amino-5-chloro-2,3-dihydro-2-(1-prop-2-enylpiperidin-4-yl)-1H-benz[de]isoquinoline-1,3-dione (0.1 g; 0.27 mmol), m.p. 279°-281° C.

Workup

  1. customthe solvent removed
  2. stirringThe residue was stirred with ammonium hydroxide and methylene chloride (50 mL)
  3. extractionThe aqueous layer was further extracted with methylene chloride (2×50 mL) and purification of the combined methylene chloride layers by column chromatography (silica gel; 3% methanol in CH2Cl2 and approximately 1% NH4OH)

Sources & evidence

ORD record
ord-7c4e6dc9bb5b4eee8ca931bc0138f180
Source dataset
uspto-grants-1993_04
Patent number
US05202318

Reaction notes

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