Piperazine → 2-(4-Phenoxybutoxy)-6-(1-Piperazinyl)Pyrazine

HRID 1296654

Reaction equation

HRID 1296654 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.O(CCCCO)C1C=CC=CC=1.[NH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C([O-])([O-])=O.[K+].[K+].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[O:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[N:3]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 5

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 2196834-Phenoxybutan-1-olHCID 181869252-Chloro-6-(4-phenoxybutoxy)pyrazineHCID 21226445Aluminium lithium hydride

Product 1

HCID 181867762-(4-Phenoxybutoxy)-6-(1-Piperazinyl)Pyrazine

Procedure

The title compound was prepared according to the procedure of example 50, step 2, starting from 2-chloro-6-(4-phenoxybutoxy)pyrazine (1.99 g, 7.14 mmol; obtained according to the procedure of example 50, step 1, starting from 4-phenoxy-1-butanol*), piperazine (1.84 g, 21.4 mmol) and K2CO3 (0.99 g, 7.14 mmol). The yield of the title compound was 1.52 g (65%) which was obtained as an oil. Purity 100% (HPLC). MS m/z 329 (M+H)+. HRMS m/z calcd for C18H24N4O2 (M)+ 328.1899, found 328.1894. *Prepared by reduction (LiAlH4) of the corresponding acid (cf J. Org. Chem. 1965, 30, 2441-2447; ibid. 1968, 33, 2271-2284).

Workup

  1. customThe title compound was prepared
  2. customobtained
  3. customwas obtained as an oil

Sources & evidence

ORD record
ord-9c078bf011934db5bb806db1888374ce
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Linked notes

Loading…