1-(3-Hydroxyphenyl)piperazine → HCID 51000678, compound

HRID 1035855Notes

Reaction equation

HRID 1035855 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([O:19][CH3:20])=[C:12]([O:17][CH3:18])[CH:13]=2)[O:8][CH:7]=1.[OH:21][C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1>>[OH:21][C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]3[C:15](=[O:16])[C:14]4[C:9](=[CH:10][C:11]([O:19][CH3:20])=[C:12]([O:17][CH3:18])[CH:13]=4)[O:8][CH:7]=3)[CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 27365971-(3-Hydroxyphenyl)piperazineHCID 67034856HCID 67034856, compound

Product 1

HCID 51000678HCID 51000678, compoundYield 17%

Procedure

Using the same starting material, 3-(4-bromobutyl)-6,7-dimethoxychromen-4-one obtained in Step 3 of Example 1, but with 3-hydroxyphenylpiperazine, and using a microwave reaction vessel (15 min, 160° C., 150 w), 3-{4-[4-(3-hydroxyphenyl)-piperazin-1-yl]-butyl}-6,7-dimethoxychromen-4-one is obtained in a similar manner to Example 1 in a yield of 17%. M.p. ° C.=177-180; analytical HPLC Sym C8, 4.6×250 mm, 5μ, eluant: CH3CN—H2O, KH2PO4 25-75-6.8 g/l, pH4, r.t.=9.99 min; MS ESI, m/z=439 (MH+); 1H NMR (CDCl3): 7.72 (s, 1H), 7.55 (s, 1H), 7.09 (t, 1H, J=8 Hz), 6.83 (s, 1H), 6.49 (d, 1H, J=8.28 Hz), 6.39 (s, 1H), 6.31 (d, 1H, J=7.84 Hz), 3.97 (s, 6H, OCH3), 3.18 (m, 4H), 2.58 (m, 4H), 2.49 (m, 2H), 2.43 (m, 2H), 1.62 (m, 4H).

Workup

  1. customa microwave reaction vessel (15 min, 160° C., 150 w)

Sources & evidence

ORD record
ord-dc8ab6b161564bdb8f10d8b302a6c439
Source dataset
uspto-grants-2013_10
Patent number
US08546402B2

Reaction notes

Loading…