Hydrochloric Acid → 6-(2-(4-(4-Quinazolinyl)piperazinyl)ethyl)-benzoxazolone hydrochloride

HRID 1935381Notes

Reaction equation

HRID 1935381 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[O:10][C:6]=2[CH:5]=1.[N:14]1([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+].[ClH:36]>O.[I-].[Na+].C(O)C>[ClH:36].[N:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:20]([N:14]2[CH2:15][CH2:16][N:17]([CH2:2][CH2:3][C:4]3[CH:13]=[CH:12][C:7]4[NH:8][C:9](=[O:11])[O:10][C:6]=4[CH:5]=3)[CH2:18][CH2:19]2)=[N:21][CH:22]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 18585334-Piperazin-1-ylquinazolineHCID 133060876-Bromoethylbenzoxazolone

Product 1

HCID 145814576-(2-(4-(4-Quinazolinyl)piperazinyl)ethyl)-benzoxazolone hydrochloride

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a 35 ml round-bottomed flask equipped with condenser and nitrogen inlet were added 1.22 grams (5.05 mmol) of 6-(2-bromoethyl)benzoxazolone, 1.08 grams (1.5 mmol) of 4-piperazinylquinazoline, 0.85 grams (8.0 mmol) of sodium carbonate, 2 mg of sodium iodide, and 35 ml of ethanol. The reaction was refluxed for 3 days, cooled, diluted with water, and the pH adjusted to 4 with 1N HCl. The aqueous layer was separated, the pH adjusted to 7 with 1N Sodium hydroxide, and the product extracted into ethyl acetate. The ethyl acetate layer was washed with brine, dried, and evaporated to give 1.3 grams of a yellow oil. The oil was crystallized from chloroform (1.1 g), dissolved in ethyl acetate, ethyl acetate saturated with hydrochloric acid gas added, and the mixture concentrated to dryness. The residue gave 0.9 grams (58%) of a yellow salt, m.p. >200° C. NMR (δ, CDCl3): 2.72 (m, 6H), 2.86 (m, 2H), 3.83 (m, 4H), 6.9-7.9 (m, 7H), 8.72 (s, 1H).

Workup

  1. customTo a 35 ml round-bottomed flask equipped with condenser and nitrogen inlet
  2. temperatureThe reaction was refluxed for 3 days
  3. temperaturecooled
  4. customThe aqueous layer was separated
  5. extractionthe product extracted into ethyl acetate
  6. washThe ethyl acetate layer was washed with brine
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-b033c0c63b62475594c46007b45e472d
Source dataset
uspto-grants-2002_05
Patent number
US06387904B2

Reaction notes

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