Hydrochloric Acid → HCID 19102635, compound

HRID 1198390Notes

Reaction equation

HRID 1198390 reaction equation
Cl.C(OC([O:7][C:8]1[CH:16]=[CH:15][C:11]2[O:12][CH2:13][O:14][C:10]=2[C:9]=1[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1)C)C>CC(O)C>[OH:7][C:8]1[CH:16]=[CH:15][C:11]2[O:12][CH2:13][O:14][C:10]=2[C:9]=1[CH2:17][N:18]1[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19102631HCID 19102631, compound

Product 1

HCID 19102635HCID 19102635, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Aqueous HCl (300 ml, 0.5N) was added to a stirred solution of 5-(1-ethoxyethoxy)-4-(4-methylpiperazinylmethyl)-1,3-benzodioxole (16.0 g, 49.7 mmol) in 2-propanol (300 ml) at room temperature, and stirring was continued for 15 minutes. The solution was extracted with diethyl ether, the aqueous layer was neutralised (pH=7) by adding aqueous NaOH(2N), and the water layer was evaporated in vacuo. The residue was extracted with diethyl ether (3 times). The combined organic layers were dried over Na2SO4, filtered and evaporated in vacuo to yield a crude oil (9.6 g). This oil was purified by flash chromatography (eluent: acetone/ethyl acetate=1/1 (v/v)) to yield 5-hydroxy-4-(4-methylpiperazinylmethyl)-1,3-benzodioxole (7.6 g, 61% yield, compound No. 8) as a solid, m.p. 85°-87° C.

Workup

  1. extractionThe solution was extracted with diethyl ether
  2. additionby adding aqueous NaOH(2N)
  3. customthe water layer was evaporated in vacuo
  4. extractionThe residue was extracted with diethyl ether (3 times)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto yield a crude oil (9.6 g)
  9. customThis oil was purified by flash chromatography (eluent: acetone/ethyl acetate=1/1 (v/v))

Sources & evidence

ORD record
ord-32583298a5884295bce49545c14e0957
Source dataset
uspto-grants-1994_01
Patent number
US05281595

Reaction notes

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