1-Phenylpiperazine → HCID 14099725, compound

HRID 569465Notes

Reaction equation

HRID 569465 reaction equation
Br[CH2:2][C:3]([C:5]1[C:9](=[CH2:10])[NH:8][CH:7]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:6]=1)=[O:4].[C:17]1([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>O1CCCC1>[CH3:10][C:9]1[NH:8][C:7]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:6][C:5]=1[C:3](=[O:4])[CH2:2][N:26]1[CH2:27][CH2:28][N:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 131715476HCID 131715476, compound

Product 1

HCID 14099725HCID 14099725, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 4 g of 2-bromo-1-[5-methyyl-2-(3-pyridinyl)-1H-imidazol-4-yl]ethanone in 50 ml of dry tetrahydrofuran was added rapidly a mixture of 2.3 g of 1-phenylpiperazine and 1.4 g of triethylamine in 5 ml of dry tetrahydrofuran. This mixture was stirred for one hour and then filtered. Evaporation of the filtrate left a gummy foam which became amorphous upon trituration with 200 ml of ether. This solid was collected, washed with ether, suspended in 6 ml of acetone and stirred for 15 minutes. The solid was collected, washed repeatedly with acetone and then dried, giving 2.6 g of the desired intermediate, mp 141°-152° C. (dec.).

Workup

  1. additionwas added rapidly
  2. filtrationfiltered
  3. customEvaporation of the filtrate
  4. waitleft a gummy foam which
  5. customThis solid was collected
  6. washwashed with ether
  7. stirringstirred for 15 minutes
  8. customThe solid was collected
  9. washwashed repeatedly with acetone
  10. customdried

Sources & evidence

ORD record
ord-f4aff4bccd5f4b77a50b09af552cb631
Source dataset
uspto-grants-1988_03
Patent number
US04732895

Reaction notes

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