Triethylamine → HCID 23045017, compound

HRID 2108105Notes

Reaction equation

HRID 2108105 reaction equation
[ClH:1].Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19])[CH2:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH2:22](N(CC)CC)C.CN(C)[C:31](=[O:33])[CH3:32].Cl.[C:36]([OH:39])(=O)[CH3:37].[C:40]([O:43][CH2:44][CH3:45])(=O)[CH3:41]>C1C=CC=CC=1.CCCCCC.O>[ClH:1].[O:43]1[C:40]2[CH:41]=[CH:22][C:37]([C:36]([N:12]3[CH2:13][CH2:14][N:9]([CH2:8][C:7]4[CH:6]=[C:5]([O:4][CH3:3])[C:17]([O:18][CH3:19])=[C:16]([O:20][CH3:21])[CH:15]=4)[CH2:10][CH2:11]3)=[O:39])=[CH:32][C:31]=2[O:33][CH2:45][CH2:44]1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 31374DimethylacetamideHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochlorideHCID 22641269Acetate-hydrochloric acid

Product 1

HCID 23045017HCID 23045017, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

A mixture of 1,4-benzodioxane-6-carboxylic acid (0.5 g), benzene (20 ml) and thionyl chloride (5 ml) is heated for one hour under reflux. The reaction mixture is evaporated to dryness under reduced pressure. To the residue is added benzene (50 ml), then the solvent is again distilled off to leave 1,4-benzodioxane-6-carbonyl chloride. This compound dissolved in benzene (20 ml) is added dropwise, while stirring, to a mixture of 1-(3,4,5trimethoxybenzyl)piperazine dihydrochloride (1 g), triethylamine (1.5 g) and N,N-dimethylacetamide (20 ml), followed by stirring at room temperature for 30 minutes. To the reaction mixture are added water (100 ml), ethyl acetate (200 ml) and hexane (50 ml), then extraction is conducted. The extract is washed with water, dried, and concentrated under reduced pressure. The residue as purified by means of a silica gel column chromatography (hexane:acetone=1:1-2:3) to afford an oily product, which is dissolved in ethyl acetate. To the solution is added 1N hydrogen chloride - acetic acid solution (5 ml), and the mixture is left standing. The supernatant is removed by decantation, and the precipitates are recrystallized from ethyl acetate to give 1-(1,4-benzodioxan-6-ylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (0.7 g) as colorless prisms, m.p. 180°-185° C.

Workup

  1. additionis added dropwise
  2. extractionextraction
  3. washThe extract is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue as purified by means of a silica gel column chromatography (hexane:acetone=1:1-2:3)
  7. customto afford an oily product, which
  8. waitthe mixture is left
  9. customThe supernatant is removed by decantation
  10. customthe precipitates are recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-450222aa24504b49951ce65db522e565
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

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