Hydrochloric Acid → HCID 23045035, compound

HRID 2108100Notes

Reaction equation

HRID 2108100 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.[ClH:14].Cl.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(P(=O)(OCC)OCC)#N.Cl>C(OCC)(=O)C.O.CN(C)C=O.C(N(CC)CC)C>[ClH:14].[ClH:14].[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([N:25]1[CH2:24][CH2:23][N:22]([CH2:21][C:20]2[CH:28]=[C:29]([O:33][CH3:34])[C:30]([O:31][CH3:32])=[C:18]([O:17][CH3:16])[CH:19]=2)[CH2:27][CH2:26]1)=[O:13]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7124Quinaldic AcidHCID 76257Diethyl cyanophosphonateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Product 1

HCID 23045035HCID 23045035, compoundYield 49.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-quinolinecarboxylic acid (0.55 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (1.1 g), triethylamine (1.2 g) and N,N-dimethylformamide (20 ml) is added dropwise at room temperature diethyl cyanophosphonate (1.2 ml), followed by stirring for one hour. After addition of water (100 ml) and ethyl acetate (100 ml), the reaction mixture is extracted with ethyl acetate. The extract is washed with water, dried, and concentrated under reduced pressure. The residue is purified by means of a silica gel column chromatography (hexane:acetone=2:1-1:1) to give an oily product, which is led to its hydrochloride, followed by crystallizing from a mixture of methanol, ethyl acetate and ethyl ether to give 1-(2-quinolylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (0.4 g) as colorless crystals, m.p. 151°-155° C.

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate
  2. washThe extract is washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by means of a silica gel column chromatography (hexane:acetone=2:1-1:1)
  6. customto give an oily product, which
  7. customby crystallizing from a mixture of methanol, ethyl acetate and ethyl ether

Sources & evidence

ORD record
ord-e29667f649a34a87ae0ab5dc1d741b1a
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

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