Hydrochloric Acid → HCID 23045030, compound

HRID 2108099Notes

Reaction equation

HRID 2108099 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.[ClH:9].Cl.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[CH2:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(P(=O)(OCC)OCC)#N.Cl>C(OCC)(=O)C.C(OCC)C.C(OCC)(=O)C.O.CN(C)C=O.C(N(CC)CC)C>[ClH:9].[C:2]1([C:6]([N:20]2[CH2:19][CH2:18][N:17]([CH2:16][C:15]3[CH:23]=[C:24]([O:28][CH3:29])[C:25]([O:26][CH3:27])=[C:13]([O:12][CH3:11])[CH:14]=3)[CH2:22][CH2:21]2)=[O:8])[S:1][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 107002-Thiophenecarboxylic acidHCID 76257Diethyl cyanophosphonateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Product 1

HCID 23045030HCID 23045030, compoundYield 50.4%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

To a mixture of thiophene-2-carboxylic acid (0.4 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (1.1 g), triethylamine (1.2 g) and dimethylformamide (20 ml) is added dropwise, while stirring, diethyl cyanophosphonate (1.2 ml), followed by stirring for one hour. To the reaction mixture are added water (100 ml) and ethyl acetate (100 ml), followed by extraction. 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) to give an oily product, which is led to its hydrochloride in a mixture of ethyl acetate - ethyl ether to yield 1-(2-thenoyl)-4(3,4,5-trimethoxybenzyl)piperazine hydrochloride (0.65 g) as colorless needles, m.p. 205°-209° C. (decomp.).

Workup

  1. additionis added dropwise
  2. stirringby stirring for one hour
  3. extractionfollowed by extraction
  4. washThe extract is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by means of a silica gel column chromatography (hexane:acetone=2:1)
  8. customto give an oily product, which

Sources & evidence

ORD record
ord-23da516c1c8044f8b194618123be7fec
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

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