Methanol → 1-Benzo[b]thiophen-4-yl-4-(3-chloropropyl)piperazine

HRID 1500556Notes

Reaction equation

HRID 1500556 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18]O)[CH2:12][CH2:11]3)=[CH:7][CH:8]=[CH:9][C:2]1=2.C(Cl)(Cl)(Cl)[Cl:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][Cl:21])[CH2:12][CH2:11]3)=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

6

Reactant 4

HCID 887MethanolHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 574825483-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)propanol

Product 1

HCID 574825511-Benzo[b]thiophen-4-yl-4-(3-chloropropyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.56 g (12.9 mmol) of 3-(4-Benzo[b]thiophen-4-yl-piperazin-1-yl)propan-1-ol was suspended in 30 ml of methylene chloride, and carbon tetrachloride (30 ml) and triphenyl phosphine (4.06 g, 15.5 mmol) were added thereto followed by stirring under reflux for 3 hours. The reaction mixture was cooled to room temperature, then methanol and methylene chloride were added thereto so as to make the mixture uniform. Silica gel (30 g) was added to the uniform solution, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (silica gel: 300 g, n-hexane:ethyl acetate=2:1), then concentrated under reduced pressure to obtain 1-benzo[b]thiophen-4-yl-4-(3-chloropropyl)piperazine (2.36 g) as colorless oil.

Workup

  1. temperatureunder reflux for 3 hours
  2. additionSilica gel (30 g) was added to the uniform solution
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (silica gel: 300 g, n-hexane:ethyl acetate=2:1)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-50d0d3229c654773b2678b9614b48ab7
Source dataset
uspto-grants-2015_12
Patent number
US09206167B2

Reaction notes

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