Potassium Carbonate → 1-(3,3-Diphenyl-propyl)-4-(4-nitro-benzyl)-[1,4]diazepane

HRID 2119342Notes

Reaction equation

HRID 2119342 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:17]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][N:13]([CH2:30][C:29]3[CH:32]=[CH:33][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=3)[CH2:12][CH2:11]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 234410351-(3,3-Diphenyipropyl)homopiperazine

Product 1

HCID 234410581-(3,3-Diphenyl-propyl)-4-(4-nitro-benzyl)-[1,4]diazepane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

The resulting 1-(3,3-diphenylpropyl )homopiperazine was dissolved in 3 mL of acetonitrile followed by adding 213 mg of 4-nitrobenzyl bromide and 144 mg of potassium carbonate. The mixture was stirred at 70° C. for 14 hours and allowed to cool to room temperature and the solvent was removed under reduced pressure. 20 mL of aqueous 2N sodium hydroxide was added and the mixture was extracted with 20 mL×2 of ethyl acetate. The organic layers were combined, washed with 20 mL of saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by column chromatography (silica gel, ethyl acetate) to obtain 255 mg of the titled compound. This was treated with a hydrogen chloride solution in ether and the solvent was removed under reduced pressure; and the residue was dried to obtain the hydrochloride salt of the titled compound.

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was removed under reduced pressure
  3. addition20 mL of aqueous 2N sodium hydroxide was added
  4. extractionthe mixture was extracted with 20 mL×2 of ethyl acetate
  5. washwashed with 20 mL of saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-b6d2b9ccf42d4f5fa0b1c36a3efc6012
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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