Water → 5-[3-(4-Diphenylmethylpiperazine-1-yl)-2-hydroxypropylthio]quinoline

HRID 1195708Notes

Reaction equation

HRID 1195708 reaction equation
Cl[CH2:2][CH:3]([OH:24])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1.[SH:25][C:26]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:27]=1[CH:28]=[CH:29][CH:30]=[N:31]2.C1CCN2C(=NCCC2)CC1.O>C(Cl)(Cl)Cl>[C:12]1([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH:3]([OH:24])[CH2:2][S:25][C:26]3[CH:35]=[CH:34][CH:33]=[C:32]4[C:27]=3[CH:28]=[CH:29][CH:30]=[N:31]4)[CH2:6][CH2:7]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 103601754-(3-Chloro-2-hydroxypropyl)-1-diphenylmethylpiperazineHCID 1357553243056-03-9

Product 1

HCID 152281355-[3-(4-Diphenylmethylpiperazine-1-yl)-2-hydroxypropylthio]quinolineYield 20.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 10 ml of chloroform were dissolved 1.2 g of 4-(3-chloro-2-hydroxypropy)-1-diphenylmethylpiperazine prepared in Example 23-(b) and 220 mg of 5-mercaptoquinoline, and 311 mg of DBU was further added thereto. Afterward, the liquid was allowed to stand at room temperature for 12 days. The reaction liquid was poured into 20 ml of water and was then extracted twice with methylene chloride. The resultant organic layer was separated, then dried with an anhydrous Glauber's salt, and was distilled off under reduced pressure. The resultant residue was purified through a silica gel chromatograph (an AcOEt effluent solvent was used) in order to obtain 130 mg of the desired compound.

Workup

  1. additionwas further added
  2. customThe reaction liquid
  3. extractionwas then extracted twice with methylene chloride
  4. customThe resultant organic layer was separated
  5. dry with materialdried with an anhydrous Glauber's salt
  6. distillationwas distilled off under reduced pressure
  7. customThe resultant residue was purified through a silica gel chromatograph (an AcOEt effluent solvent

Sources & evidence

ORD record
ord-a19f032918a74e80a5b574747c5bbf9f
Source dataset
uspto-grants-1992_05
Patent number
US05112817

Reaction notes

Loading…