Ethyl 4-bromobutyrate → Ethyl 4-[4-(2-methoxyphenyl)piperazin-1-yl]butanoate

HRID 887061Notes

Reaction equation

HRID 887061 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]1[CH2:24][CH2:23][N:22]([CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 76300Ethyl 4-bromobutyrateHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochloride

Product 1

HCID 11370225Ethyl 4-[4-(2-methoxyphenyl)piperazin-1-yl]butanoate

Procedure

Ethyl 4-(4-(2-methoxyphenyl)piperazin-1-yl)butanoate (17c) (Scheme 3) was synthesized from ethyl 4-bromobutanoate 16 and the piperazine 4 (R12═OMe, R13═H) according to protocol described for 17a (Example 19). Brown oil, 9.6 g (99%). 1H NMR (400 MHz, CDCl3): δ 1.23 (t, J=7.2 Hz, 3H), 1.82 (quintet, J=7.2 Hz, 2H); 2.35 (t, J=7.2 Hz, 2H); 2.43 (t, J=7.2 Hz, 2H); 2.63 (broad s, 4H); 3.07 (broad s, 4H); 3.84 (s, 3H); 4.13 (q, J=7.2 Hz, 2H); 6.83-6.99 (m, 4H). MS (ESI): m/z=307.50 (M+H+).

Sources & evidence

ORD record
ord-09e931f839fb49b29385c8e06ec6c5c9
Source dataset
uspto-grants-2012_08
Patent number
US08247420B2

Reaction notes

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