Quinone → HCID 10007683, compound

HRID 733485Notes

Reaction equation

HRID 733485 reaction equation
[C:1]1(=[O:8])[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.[CH2:9]([N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH2:12][CH2:13][CH2:14][NH2:15])[CH3:10]>CO>[CH2:9]([N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH2:12][CH2:13][CH2:14][NH:15][C:6]1[C:1](=[O:8])[CH:2]=[C:3]([NH:15][CH2:14][CH2:13][CH2:12][N:11]([CH2:9][CH3:10])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[C:4](=[O:7])[CH:5]=1)[CH3:10]

Participants

4

Reactant 2

HCID 4650QuinoneHCID 23625665HCID 23625665, compound

Product 1

HCID 10007683HCID 10007683, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of p-benzoquinone (0.1 g; 0.92 mmol) in 70 ml of MeOH was added when cold N1-ethyl-N1-(2-methoxy-benzyl)-propan-1,3-diamine (0.45 g; 2.0 mmol). The reaction mixture was agitated at e.t. and out of the light for 6 h, the was evaporated in a vacuum to give a crude material which was purified by flash chromatography. Eluting with CH2Cl2/MeOH/NH4OH 9.75:0.25:0.025 obtained 0.23 g of the compound XII as a pure red solid on TLC (eluant: CHCl3/MeOH/NH4OH 9.5:0.5:0.05). Yield 45%; 1H NMR (free base; CDCl3) δ: 1.11 (t, 6H), 1.72-1.85 (m, 4H), 2.56 (q, 8H), 3.18 (q, 4H), 3.62 (s, 4H), 3.82 (s, 6H), 5.26 (s, 2H), 6.83-6.95 (m, 4H), 7.19-7.43 (m, 4H+2H exchangeable with D2O); EI-MS: m/z=548 (M+).

Workup

  1. customthe was evaporated in a vacuum
  2. customto give a crude material which
  3. customwas purified by flash chromatography
  4. washEluting with CH2Cl2/MeOH/NH4OH 9.75:0.25:0.025

Sources & evidence

ORD record
ord-6872801fd4bb44d7b01289d576ddd9e5
Source dataset
uspto-grants-2009_09
Patent number
US07589219B2

Reaction notes

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