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

HRID 493338Notes

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-a7e607b9f6cc4b518a2e63fa02794200
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534794B2

Reaction notes

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