Hydrochloric Acid → 1-(2-Indanylcarbonyl)-4-(3,4,5-trimethoxybenzyl)-piperazine hydrochloride

HRID 1638794Notes

Reaction equation

HRID 1638794 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=O.C1C2C(=CC=CC=2)CC1C([Cl:24])=O.S(Cl)(Cl)=O.Cl.Cl.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:43]=[C:44]([O:48][CH3:49])[C:45]=1[O:46][CH3:47])[CH2:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.Cl>C1(C)C=CC=CC=1.CO.C(OCC)(=O)C.O.CN(C)C=O.C(N(CC)CC)C>[ClH:24].[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[C:10]([N:40]1[CH2:39][CH2:38][N:37]([CH2:36][C:35]2[CH:43]=[C:44]([O:48][CH3:49])[C:45]([O:46][CH3:47])=[C:33]([O:32][CH3:31])[CH:34]=2)[CH2:42][CH2:41]1)=[O:12]

Participants

12

Reactant 5

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 5757772-Indancarboxylic AcidHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochlorideHCID 213133822,3-dihydro-1H-indene-2-carbonyl chloride

Product 1

HCID 198412021-(2-Indanylcarbonyl)-4-(3,4,5-trimethoxybenzyl)-piperazine hydrochloride

Reagents, catalysts & solvents 6

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

In a manner as that described in Example 5, 2-indane carboxylic acid (0.8 g) is converted to the 2-indane carbonyl chloride by using thionyl chloride (2 ml) in toluene (10 ml). The product thus obtained is added to a mixture of 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (2.1 g), triethylamine (5.9 g) and N,N-dimethylformamide (20 ml). The whole mixture is left standing at room temperature for two hours. A mixture of water (300 ml) and ethyl acetate (300 ml) is added to the mixture, and the mixture is shaken thoroughly. The organic layer is separated, washed with water, dried and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (hexane:acetone=1:1) to give an oily product, which is converted to the hydrochloride in a mixture of methanol and ethyl acetate to give 1-(2-indanylcarbonyl)-4-(3,4,5-trimethoxybenzyl)-piperazine hydrochloride (1.1 g) as colorless crystals, m.p. 227°-232° C. (decomp.).

Workup

  1. customThe product thus obtained
  2. waitThe whole mixture is left
  3. additionis added to the mixture
  4. customThe organic layer is separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (hexane:acetone=1:1)
  9. customto give an oily product, which

Sources & evidence

ORD record
ord-b3ad8c61b3d04cc79b38144376a4cb1b
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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