Hydrochloric Acid → HCID 67706187, compound

HRID 1379186Notes

Reaction equation

HRID 1379186 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].[C:30](Cl)(=[O:39])/[CH:31]=[CH:32]/[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl>CN(C)C=O.ClCCl.O1CCOCC1.O>[C:30]([N:11]1[CH2:12][CH2:13][NH:8][C@H:9]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:10]1)(=[O:39])/[CH:31]=[CH:32]/[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 5354261Cinnamoyl ChlorideHCID 51387188HCID 51387188, compound

Product 1

HCID 67706187HCID 67706187, compoundYield 60.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred mixture of (2R)-1-(tert-butoxycarbonyl)-2-(1H-indol-3-yl-methyl)piperazine (250 mg) and potassium carbonate (165 mg) in dimethylformamide (1 ml) was added trans-cinnamoyl chloride (150 mg) at room temperature. The resulting mixture was stirred for 3 hours and then poured into water. Extraction with ethyl acetate followed by drying over magnesium sulfate and evaporation in vacuo gave a syrup, which was dissolved in dichloromethane (2 ml). A solution of 4N hydrogen chloride in dioxane solution (1 ml) was added to the solution at ice-bath temperature and the resulting mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and aqueous saturated sodium bicarbonate solution. The organic layer was separated, washed with brine and dried over magnesium sulfate. Evaporation of the solvent in vacuo gave (3R)-1-(trans-cinnamoyl)-3-(1H-indol-3-yl-methyl)piperazine (166 mg).

Workup

  1. extractionExtraction with ethyl acetate
  2. dry with materialby drying over magnesium sulfate and evaporation in vacuo
  3. customgave a syrup, which
  4. stirringthe resulting mixture was stirred for 1 hour at room temperature
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customThe residue was partitioned between ethyl acetate and aqueous saturated sodium bicarbonate solution
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over magnesium sulfate
  10. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-28db43ecfef44690b33a4f690942d49b
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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