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

HRID 1907365Notes

Reaction equation

HRID 1907365 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>ClCCl>[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 dichloromethane, and carbon tetrachloride (30 ml) and triphenyl phosphine (4.06 g, 15.5 mmol) were added thereto. The mixture was refluxed with heating for 3 hours. The reaction solution was cooled to room temperature, then methanol and dichloromethane were added thereto to homogenize the mixture. Silica gel (30 g) was added to the solution, and the solvent was evaporated under reduced pressure. The obtained residue was loaded on silica gel column (300 g) and extracted with a solvent mixture of n-hexane:ethyl acetate=2:1. The extraction solution was concentrated under reduced pressure to obtain 1-benzo[b]thiophen-4-yl-4-(3-chloropropyl)piperazine (2.36 g) as colorless oil.

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating for 3 hours
  3. additionSilica gel (30 g) was added to the solution
  4. customthe solvent was evaporated under reduced pressure
  5. extractionextracted with a solvent mixture of n-hexane
  6. concentrationThe extraction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a2054310a9324b3793cdeb8143a4eeea
Source dataset
uspto-grants-2013_12
Patent number
US08598162B2

Reaction notes

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