Hydrochloric Acid → HCID 67623008, compound

HRID 1769684Notes

Reaction equation

HRID 1769684 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:20])[CH2:11][N:12]1[CH2:17][CH2:16][N:15](C=[O:19])[CH2:14][CH2:13]1.[ClH:21]>CO>[OH2:19].[ClH:21].[ClH:21].[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C:10](=[O:20])[CH2:11][N:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53725875HCID 53725875, compound

Product 1

HCID 67623008HCID 67623008, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(2,6-dimethylphenyl)-4-formyl-1-piperazineacetamide (17.70 g, 64.0 mmol) was dissolved in a mixture of methanol (500 mL) and 1N HCl (130 mL) under nitrogen. The mixture was refluxed for 7 h before it was cooled, concentrated and partitioned between ethyl acetate and water. The aqueous phase was then separated away from the organic phase and evaporated down to dryness. There was isolated 21.00 g (98%) of the title compound as a white solid, m.p. 185°-195° C. (sealed tube); 1H NMR (300 MHz, D2O) δ 7.11-7.01 (m, 3H), 4.31 (s, 2H), 3.65-3.62 (m, 4H), 3.56-3.50 (m, 4H), 2.04 (s, 6H); 13C NMR (75 MHz, D2O) ppm 168.55, 140.74, 136.95, 133.37, 133.19, 61.89, 54.16, 45.56, 22.24; IR (KBr) 3440, 2958, 1690, 1532, 1472, 1442, 1386, 1308, 1240, 964, 770 cm-1 ; MS m/z calc'd for C14H22N3O 248.1763, found 248.1763.

Workup

  1. temperatureThe mixture was refluxed for 7 h before it
  2. temperaturewas cooled
  3. concentrationconcentrated
  4. custompartitioned between ethyl acetate and water
  5. customThe aqueous phase was then separated away from the organic phase
  6. customevaporated down to dryness
  7. customThere was isolated

Sources & evidence

ORD record
ord-c92ab4695e0f4fd6a75cb1fe0f685049
Source dataset
uspto-grants-1995_01
Patent number
US05382584

Reaction notes

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