1-(2-Methoxyphenyl)piperazine → HCID 66881744, compound

HRID 1876827Notes

Reaction equation

HRID 1876827 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])[CH2:18][CH2:17]2)=[O:15])=[C:8]([N+:30]([O-:32])=[O:31])[CH:7]=1.[CH3:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:13][O:12][C:11]1[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:44]2[CH2:43][CH2:42][N:41]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[O:34][CH3:33])[CH2:46][CH2:45]2)=[CH:7][C:8]([N+:30]([O-:32])=[O:31])=[C:9]([C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])[CH2:18][CH2:17]2)=[O:15])[CH:10]=1

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 11430Potassium CarbonateHCID 66882500HCID 66882500, compound

Product 1

HCID 66881744HCID 66881744, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of [4-(3-bromopropyloxy)-5-methoxy-2-nitrophenyl][4-(2-methoxyphenyl)piperazino]methanone (9) (500 mg, 1.65 mmol), 1-(2-methoxyphenyl)piperazine (316 mg 15.6 mmol) and K2CO3 (816 mg 26.6 mmol) in acetone (30 mL) and the stirring was continued for 16 h. The acetone was evaporated in vacuum and the aqueous layer was washed with ethyl acetate and extracted with ethyl acetate and washed with brine, dried over Na2SO4 and evaporated in vacuum to afford the crude product to (5-methoxy-4-3-[4-(2-methoxyphenyl)-piperazino]propoxy-2-nitrophenyl)[4-(2-methoxyphenyl)piperazino]methanone (10) in 93% yield (670 mg, 85% yield). 1H NMR (CDCl3): δ 1.60-2.15 (m, 2H), 2.98-3.12 (t, 2H, J=7.31 Hz), 3.18-3.36 (m, 8H), 3.38-3.60 (m, 10H), 3.85 (m, 3H), 3.95 (s, 3H), 4.00-4.15 (m, 3H) 6.85-7.00 (m, 8H), 7.20-7.40 (m, 1H), 7.70-7.80 (d, 1H, J=6.81 Hz); FABMS: 619 (M+H)+.

Workup

  1. customThe acetone was evaporated in vacuum
  2. washthe aqueous layer was washed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuum

Sources & evidence

ORD record
ord-9670291fc0e84b1ab8ba58db096f840d
Source dataset
uspto-grants-2012_11
Patent number
US08309726B2

Reaction notes

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