Phenethyl bromide → 3-[4-(2-Phenylethyl)piperazin-1-yl-]1-[2-(2,4,5-trifluorophenoxy)ethyl]pyrazin-2(1H)-one, Hydrochloride

HRID 1295723Notes

Reaction equation

HRID 1295723 reaction equation
[N:1]1([C:7]2[C:8](=[O:25])[N:9]([CH2:13][CH2:14][O:15][C:16]3[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=3[F:24])[CH:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[ClH:26].N1(C2C(=O)N(CCOC3C=C(F)C(F)=CC=3F)C=CN=2)CCNCC1.Br[CH2:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>>[ClH:26].[C:55]1([CH2:54][CH2:53][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[C:8](=[O:25])[N:9]([CH2:13][CH2:14][O:15][C:16]4[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=4[F:24])[CH:10]=[CH:11][N:12]=3)[CH2:2][CH2:3]2)[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

4

Reactant 3

HCID 7666Phenethyl bromideHCID 104058482(1H)-Pyrazinone, 3-(1-piperazinyl)-1-[2-(2,4,5-trifluorophenoxy)ethyl]-HCID 116397093-(1-Piperazinyl)-1-[2-(2,4,5-trifluorophenoxy)ethyl]-2(1H)-pyrazinone, Hydrochloride

Product 1

HCID 100514513-[4-(2-Phenylethyl)piperazin-1-yl-]1-[2-(2,4,5-trifluorophenoxy)ethyl]pyrazin-2(1H)-one, Hydrochloride

Procedure

The title compound was prepared according to the procedure of Example 60 starting from 3-(1-piperazinyl)-1-[2-(2,4,5-trifluorophenoxy)ethyl]-2(1H)-pyrazinone (0.71 g, 2.0 mmol; from the free base of Example 3) and (2-bromoethyl)benzene (0.41 g, 2.2 mmol). Yield: 0.20 g (20%). HPLC purity: 96%. HRMS calc for C24H25F3N4O2 (M)+ 458.1930, found 458.1928.

Sources & evidence

ORD record
ord-b5332316ce2f4ec6b0552eccf298c207
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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