Piperazine → 1-(1-Benzothiophen-4-yl)piperazine hydrochloride

HRID 1500543Notes

Reaction equation

HRID 1500543 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C1([B-](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C(C)=CC=CC=1>[ClH:1].[N:11]1([C:2]2[C:10]3[CH:9]=[CH:8][S:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 4837PiperazineHCID 123986054-Chloro-1-benzothiopheneHCID 23136663Tri-tert-butylphosphonium TetraphenylborateHCID 23676156Sodium t-butoxide

Product 1

HCID 574825411-(1-Benzothiophen-4-yl)piperazine hydrochloride

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

4-Chlorobenzo[b]thiophene (5.00 g), piperazine (5.11 g), palladium acetate (II) (2.7 mg), tri-tert-butylphosphonium tetraphenylborate (6.2 mg), sodium tert-butoxide (8.548 g), and xylene (70 ml) were stirred at 120 to 130° C. for 5 hours. After the reaction mixture was cooled to room temperature, water was added thereto, and the layers were separated. The xylene layer was washed with water, and then with saline. After addition of activated carbon, the mixture was stirred at room temperature for 30 minutes. After filtration of the mixture, concentrated hydrochloric acid was added to the filtrate, and the resulting mixture was stirred at room temperature for 30 minutes. The precipitated crystals were collected by filtration and dried to obtain 4-(1-piperazinyl)benzo[b]thiophene hydrochloride.

Workup

  1. customthe layers were separated
  2. washThe xylene layer was washed with water
  3. additionAfter addition of activated carbon
  4. filtrationAfter filtration of the mixture, concentrated hydrochloric acid
  5. additionwas added to the filtrate
  6. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  7. filtrationThe precipitated crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-3d1138d97cb1485ca7def65d04daf19c
Source dataset
uspto-grants-2015_12
Patent number
US09206169B2

Reaction notes

Loading…