Hydrochloric Acid → HCID 20267917, compound

HRID 1719218Notes

Reaction equation

HRID 1719218 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7]1.Cl[CH2:32][C:33](=[O:40])[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].Cl>O1CCCC1.C(O)(C)C>[CH2:38]([O:37][C:35]([CH2:34][C:33]([CH2:32][O:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:10][CH2:11]1)=[O:40])=[O:36])[CH3:39]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetateHCID 20267913HCID 20267913, compound

Product 1

HCID 20267917HCID 20267917, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

0.9 g of Sodium hydride was added to 15 ml of dry tetrahydrofuran stirring at room temperature under nitrogen. A solution of 1-(2-hydroxyethyl)-4-triphenylmethylpiperazine in 5 ml of dry tetrahydrofuran was added dropwise and then stirred a further 1 hour after the addition was complete. Finally, a solution of 1.8 g of ethyl 4-chloroacetoacetate in 5 ml of dry tetrahydrofuran was added over 1 hour and the mixture stirred at room temperature for 18 hours. 5 Drops of isopropanol were added to the mixture which was then poured onto 100 g of ice and carefully neutralised with concentrated hydrochloric acid. After extraction with ethyl acetate, the residual oil was dissolved in acetonitrile, washed three times with petroleum ether (40°-60°) and evaporated to give 2.6 g of 1-[2-(ethoxycarbonylacetylmethoxy)ethyl]-4-triphenylmethylpiperazine as an orange-red oil, used directly.

Workup

  1. additionafter the addition
  2. stirringthe mixture stirred at room temperature for 18 hours
  3. extractionAfter extraction with ethyl acetate
  4. dissolutionthe residual oil was dissolved in acetonitrile
  5. washwashed three times with petroleum ether (40°-60°)
  6. customevaporated

Sources & evidence

ORD record
ord-1cc81511f054423fbd45290011883250
Source dataset
uspto-grants-1985_09
Patent number
US04539322

Reaction notes

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