Acetic Acid → HCID 19102631, compound

HRID 1198389Notes

Reaction equation

HRID 1198389 reaction equation
[BH3-]C#N.[Na+].[CH2:5]([O:7][CH:8]([O:10][C:11]1[CH:19]=[CH:18][C:14]2[O:15][CH2:16][O:17][C:13]=2[C:12]=1[CH:20]=O)[CH3:9])[CH3:6].[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(O)(=O)C>CC#N>[CH2:5]([O:7][CH:8]([O:10][C:11]1[CH:19]=[CH:18][C:14]2[O:15][CH2:16][O:17][C:13]=2[C:12]=1[CH2:20][N:26]1[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]1)[CH3:9])[CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5003444Sodium cyanoborohydrideHCID 19102630HCID 19102630, compound

Product 1

HCID 19102631HCID 19102631, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NaCNBH3 (6.4 g, 101.8 mmol) was added to a stirred solution of 5-(1-ethoxyethoxy)-4-formyl-1,3-benzodioxole (16.0 g, 67.2 mmol) and 1-methylpiperazine (20.2 g, 201.7 mmol) in CH3CN (150 ml). Acetic acid (10 ml) was added dropwise to the solution in one hour at room temperature, to keep the pH neutral (pH=7). After 3 hours of additional stirring, most of the CH3CN was evaporated in vacuo. Aqueous NaOH (2N, 300 ml) was added and the resulting mixture was extracted with diethyl ether (3 times). The combined ether extracts were washed with an aqueous solution of Na2CO3, dried over Na2SO4, filtered and evaporated to yield 26 g of a crude oil. This oil was purified by flash chromatography (eluent gradient; dichloromethane/methanol/25% aqueous ammonia=95/4.5/0.5 to 85/14/1 (v/v) to give 5-(1-ethoxyethoxy)-4-(4-methyl-piperazinylmethyl)-1,3-benzodioxole (16.0 g, 74% yield, compound No. 4) as a colorless oil.

Workup

  1. custommost of the CH3CN was evaporated in vacuo
  2. additionAqueous NaOH (2N, 300 ml) was added
  3. extractionthe resulting mixture was extracted with diethyl ether (3 times)
  4. washThe combined ether extracts were washed with an aqueous solution of Na2CO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto yield 26 g of a crude oil
  9. customThis oil was purified by flash chromatography (eluent gradient

Sources & evidence

ORD record
ord-a220ade3a346465998777390eabed5c1
Source dataset
uspto-grants-1994_01
Patent number
US05281595

Reaction notes

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