1-Benzylpiperazine → HCID 18377471, compound

HRID 1736094Notes

Reaction equation

HRID 1736094 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][N:5]=1.[CH2:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C(C)=CC=CC=1.C(Cl)Cl>[ClH:1].[ClH:1].[C:14]1([CH2:13][N:20]2[CH2:21][CH2:22][N:23]([CH2:2][CH2:3][C:4]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[O:6][N:5]=3)[CH2:24][CH2:25]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 759941-BenzylpiperazineHCID 12279145HCID 12279145, compound

Product 1

HCID 18377471HCID 18377471, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-(2-chloroethyl)-1,2-benzisoxazole (0.55 g, 3.03 mmol) and N-benzylpiperazine (1.06 mL, 6.06 mmol) in xylene (4 mL) was heated at 150° C. for 4.75 hours. The cooled mixture was diluted with CH2Cl2 and washed with H2O. The organic layer was dried (MgSO4), filtered and concentrated. Purification by silica gel flash chromatography (50% EtOAc-hexanes→100% EtOAc) gave the title compound, free base (0.337 g, 35%) as a pale yellow oil.

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel flash chromatography (50% EtOAc-hexanes→100% EtOAc)

Sources & evidence

ORD record
ord-656e789030684e61b0335cb2677d74b2
Source dataset
uspto-grants-1996_07
Patent number
US05538984

Reaction notes

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