Dichloromethane → HCID 57499597, compound

HRID 1907389Notes

Reaction equation

HRID 1907389 reaction equation
C(N(CC)CC)C.[Cl:8]CCl.[S:11]1[CH:15]=[CH:14][C:13]2[C:16]([N:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][O:29][CH:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)[CH2:22][CH2:21]3)=[CH:17][CH:18]=[CH:19][C:12]1=2.[C:36](Cl)(=[O:38])[CH3:37]>O>[ClH:8].[S:11]1[CH:15]=[CH:14][C:13]2[C:16]([N:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][O:29][CH:30]4[CH2:35][CH2:34][N:33]([C:36](=[O:38])[CH3:37])[CH2:32][CH2:31]4)[CH2:22][CH2:21]3)=[CH:17][CH:18]=[CH:19][C:12]1=2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 53630738HCID 53630738, compound

Product 1

HCID 57499597HCID 57499597, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (0.28 ml, 2.0 mmol) was added to a dichloromethane solution (15 ml) of 1-benzo[b]thiophen-4-yl-4-[3-(piperidin-4-yloxy)-propyl]-piperazine (0.45 g, 1.25 mmol) and the mixture was cooled in an ice bath. To this, acetyl chloride (0.1 ml, 1.4 mmol) was added and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, which was then extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and thereafter concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1). The purified product was concentrated under reduced pressure. To the residue, 0.5 N hydrochloride-methanol solution (3 ml) was added. The crystal produced was obtained by filtration and dried to obtain 1-benzo[b]thiophen-4-yl-4-[3-(1-acetylpiperidin-4-yloxy)propyl]piperazine hydrochloride as white powder (0.36 g, 66% yield).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. extractionwas then extracted with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1)
  6. concentrationThe purified product was concentrated under reduced pressure
  7. additionTo the residue, 0.5 N hydrochloride-methanol solution (3 ml) was added
  8. customThe crystal produced
  9. customwas obtained by filtration
  10. customdried

Sources & evidence

ORD record
ord-de83cd6144454df18277c10dfee1f57f
Source dataset
uspto-grants-2013_12
Patent number
US08598162B2

Reaction notes

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