Hydrochloric Acid → HCID 23045031, compound

HRID 2108102Notes

Reaction equation

HRID 2108102 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.[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.O.CN(C)C=O.C(N(CC)CC)C>[ClH:9].[CH:2]1[S:1][CH:5]=[CH:4][C:3]=1[C:6]([N:20]1[CH2:19][CH2:18][N:17]([CH2:16][C:15]2[CH:23]=[C:24]([O:28][CH3:29])[C:25]([O:26][CH3:27])=[C:13]([O:12][CH3:11])[CH:14]=2)[CH2:22][CH2:21]1)=[O:8]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6918Thiophene-3-carboxylic acidHCID 76257Diethyl cyanophosphonateHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Product 1

HCID 23045031HCID 23045031, compoundYield 46.6%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-thiophenecarboxylic acid (0.2 g), 1(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (0.56 g), triethylamine (0.6 g) and N,N-dimethylforamide (10 ml) is added dropwise at room temperature diethyl cyanophosphonate (0.6 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) to give an oily product, which is led to its hydrochloride, followed by crystallization from a mixture of ethyl acetate and ethyl ether to afford 1-(3-thenoyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (0.3 g) as colorless needles, m.p. 201°-205° C. (decomp.).

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)
  6. customto give an oily product, which
  7. customfollowed by crystallization from a mixture of ethyl acetate and ethyl ether

Sources & evidence

ORD record
ord-fa1bcb0f3b8a432d8e2b02589c7a2e59
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

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