1-(2-Methoxyphenyl)piperazine → Piperazine, 1-(3-((3,4-dihydro-2H-1-benzothiopyran-8-yl)oxy)-1-oxopropyl)-4-(2-methoxyphenyl)-

HRID 274747Notes

Reaction equation

HRID 274747 reaction equation
[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:12][CH2:13][C:14]([OH:16])=O)[CH2:4][CH2:3][CH2:2]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1>CN(C)C=O>[CH3:39][O:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[N:47]1[CH2:52][CH2:51][N:50]([C:14](=[O:16])[CH2:13][CH2:12][O:11][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[S:1][CH2:2][CH2:3][CH2:4]3)[CH2:49][CH2:48]1

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20093609HCID 20093609, compound

Product 1

HCID 3073923Piperazine, 1-(3-((3,4-dihydro-2H-1-benzothiopyran-8-yl)oxy)-1-oxopropyl)-4-(2-methoxyphenyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 110 mg (4.61×10-4 mol) of 3-[(thiochroman-8-yl)oxy]propionic acid (Indian Journal of Chemistry (1977) 15 pp. 715-719) are dissolved in 1.5 cm3 of dimethylformamide. The flask is cooled in an ice-bath. 100 mg (5.07×10-4 mol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 71 mg (4.61×10-4 mol) of 1-hydroxybenzotriazole and 100 mg (5.07×10-4 mol) of 1-(2-methoxyphenyl)piperazine are added. The mixture is allowed to come gradually to room temperature. After 24 hours, the solvent is evaporated off. The residue is taken up in H2O and extracted with CH2Cl2. The product is dried over MgSO4.

Workup

  1. temperatureThe flask is cooled in an ice-bath
  2. customto come gradually to room temperature
  3. customthe solvent is evaporated off
  4. extractionextracted with CH2Cl2
  5. dry with materialThe product is dried over MgSO4

Sources & evidence

ORD record
ord-fc153236807c4d2c9989f1d0b940ce99
Source dataset
uspto-grants-1995_02
Patent number
US05389668

Reaction notes

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