Hydrochloric Acid → HCID 13362828, compound

HRID 1290881Notes

Reaction equation

HRID 1290881 reaction equation
C1O[C:4]([CH2:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)([CH3:5])[O:3]C1.Cl>C1COCC1>[CH:15]([N:12]1[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][CH2:6][C:4](=[O:3])[CH3:5])[CH2:14][CH2:13]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13864615HCID 13864615, compound

Product 1

HCID 13362828HCID 13362828, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(4-benzhydrylpiperazin-1-yl)-2-pentanone ethylene ketal (1.10 g, 2.9 mmol) in THF (25 ml) was treated with concentrated hydrochloric acid (2 ml) and stirred at room temperature overnight. The reaction mixture was evaporated to dryness before partitioning between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulphate, filtered and concentrated to yield 5-(4-benzhydrylpiperazin-1-yl)-2-pentanone as a colourless oil (716 mg, 80%).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custombefore partitioning between ethyl acetate and saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-456b46b0ce9143178faf270df3f21001
Source dataset
uspto-grants-1998_05
Patent number
US05753671

Reaction notes

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