1-Chloroanthraquinone → 1-{[2-(2-Hydroxymethylpyrrolidin-1-yl)ethyl]amino}-anthracene-9,10-dione

HRID 226253

Reaction equation

HRID 226253 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:9][OH:10].Cl[C:12]1[C:25]2[C:24](=[O:26])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:27])[C:16]=2[CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[OH:10][CH2:9][CH:5]1[CH2:6][CH2:7][CH2:8][N:4]1[CH2:3][CH2:2][NH:1][C:19]1[C:18]2[C:17](=[O:27])[C:16]3[C:25](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:24](=[O:26])[C:23]=2[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 67091-ChloroanthraquinoneHCID 21283823[1-(2-Amino-ethyl)-pyrrolidin-2-yl]-methanol

Product 1

HCID 119945131-{[2-(2-Hydroxymethylpyrrolidin-1-yl)ethyl]amino}-anthracene-9,10-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

To [1-(2-aminoethyl)-pyrrolidin-2-yl-]methanol (1.63 g, 11.3 mmol) in pyridine (10 mL) was added 1-chloroanthraquinone (1.37 g, 5.646 mmol), and the mixture was stirred at 65° C. for 24 hours. Pyridine was removed in vacuo and the resulting mixture of oil and solid was dissolved in CH2Cl2 and washed with H2O (3×50 mL) to remove any unreacted amine. The separated organic layer was removed in vacuo and the crude product was chromatographed using CH2Cl2/CH3OH (97:3). The desired product was yielded as a red powder (0.21 g, 11%). M.p. 113-115° C.; δH(250 MHz; CDCl3); 1.75-2.0 (m, 4H), 2.25-2.35 (m, 1H), 2.6-2.8 (m, 2H), 3.15-3.3 (m, 2H), 3.35-3.55 (m, 4H), 3.75-3.85 (2×d, 1H), 7.0 (2×d, 1H), 7.45-7.6 (m, 2H), 7.65-7.8 (m, 2H), 8.2 (2×d, H), 8.45 (2×d), and 10.05 (s, 1H, C(1)NH); δC(62.9 MHz; CDCl3); 24.11, 27.15, 41.64, 52.99, 53.82, 62.61, 65.26, 113.15, 115.60, 126.57, 132.86, 133.81, 135.32, 151.49, 183.77, and 184.89; FAB MS, m/z(M+H)+ 351; Anal. calcd for C21H22N2O3: C, 71.98; H, 6.33; N, 8.00. Found: C, 71.79; H, 6.13; N, 8.07.

Workup

  1. customPyridine was removed in vacuo
  2. additionthe resulting mixture of oil and solid
  3. dissolutionwas dissolved in CH2Cl2
  4. washwashed with H2O (3×50 mL)
  5. customto remove any unreacted amine
  6. customThe separated organic layer was removed in vacuo
  7. customthe crude product was chromatographed

Sources & evidence

ORD record
ord-ed6c0dc621a74869b63584026e5e155b
Source dataset
uspto-grants-2009_07
Patent number
US07557215B2

Linked notes

Loading…