Piperazine, hexahydrate → 1-[3-(2-Phenoxyethoxy)-2-pyridinyl]piperazine, Dihydrochloride

HRID 1789752Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.O.O.O.O.O.O.[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>O>[ClH:1].[ClH:1].[O:11]([CH2:10][CH2:9][O:8][C:7]1[C:2]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[N:3][CH:4]=[CH:5][CH:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 165 °C

Procedure

A mixture of the product from Step 1 above (0.84 g, 3.1 mmol) and piperazine hexahydrate (5.3 g, 27.3 mmol) was heated in a sealed tube at 165° C. for 1 h. After cooling, the mixture was diluted with water (100 mL) and extracted twice with EtOAc. The combined and dried (MgSO4) organic phases were concentrated in vacuo and the residue was purified by chromatography on silica gel using CHCl3/MeOH/NH4OH (90:10:0.4) as eluent to give the free base of the title compound. The free base was treated with HCl/ether, and the resulting dihydrochloride salt was dried (80° C., 1 mmHg) to afford 0.598 g (52%) of the title compound as a light yellow solid: mp 91-120° C. Anal. (C17H21N3O2.2HCl) C, H, N.

Workup

temperatureAfter cooling
extractionextracted twice with EtOAc
dry with materialdried (MgSO4) organic phases
concentrationwere concentrated in vacuo
customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-28325c9c9feb493b8fdcc874c61df9d2
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071180B2

Reaction notes

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