Hydrogen Bromide → HCID 20162901, compound

HRID 246821Notes

Reaction equation

HRID 246821 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]([CH:18]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[N:8]=2)=[CH:4][CH:3]=1.Br.C([O-])([O-])=O.[K+].[K+].[CH3:34][O:35][CH2:36][CH2:37]Cl>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]([CH:18]3[CH2:24][CH2:23][CH2:22][N:21]([CH:36]([O:35][CH3:34])[CH3:37])[CH2:20][CH2:19]3)[N:8]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl etherHCID 1625582-(Azepan-4-yl)-4-[(4-chlorophenyl)methyl]phthalazin-1(2H)-one

Product 1

HCID 20162901HCID 20162901, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

6 grams (0.013 mole) of 4-(4-chlorobenzyl)-2-(hexahydroazepin-4-yl)-1-(2H)-phthalazinone× HBr were stirred together with 3.6 grams (0.026 mole) of K2CO3, 7.4 grams (0.078 mole=7.1 ml) of 2-chloroethyl methyl ether and 30 ml of dimethylacetamide for 21/2 hours at an oil bath temperature of 120° C. Subsequently the mixture was cooled to room temperature and filtered off with suction from the insolubles. The solution was concentrated in a vacuum and the brownish oil obtained chromatographed by means of a silica gel column (elution agent: CH2Cl2 /CH3OH=90:10). The desired fractions were combined and the solvent distilled off on the rotary evaporator. The oily residue was made acid with isopropanol/HCl. The hydrochloride was precipitated as a viscous mass by addition of ether. After decanting off the supernatant solution the residue was triburated with methyl ethyl ketone at boiling heat, whereby the desired hydrochloride was obtained as a crystalline product. M.P. 194°-197° C. Yield: 1.8 grams (28%).

Workup

  1. filtrationfiltered off with suction from the insolubles
  2. concentrationThe solution was concentrated in a vacuum
  3. customthe brownish oil obtained
  4. customchromatographed by means of a silica gel column (elution agent: CH2Cl2 /CH3OH=90:10)
  5. distillationthe solvent distilled off on the rotary evaporator
  6. customThe hydrochloride was precipitated as a viscous mass by addition of ether
  7. customAfter decanting off the supernatant solution the residue
  8. temperatureat boiling heat

Sources & evidence

ORD record
ord-86eb826b414d4c08ae4e12647deef755
Source dataset
uspto-grants-1987_11
Patent number
US04704387

Reaction notes

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