Hydrochloric Acid → HCID 67229171, compound

HRID 448361Notes

Reaction equation

HRID 448361 reaction equation
[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[C:15](=[O:31])[N:16]([CH:23]2[CH2:28][CH2:27][C:26](=[O:29])[NH:25][C:24]2=[O:30])[C:17]3=[O:22])=[C:8]([O:32][CH3:33])[CH:7]=1.[ClH:35]>C(Cl)Cl.CO.CCOCC>[ClH:35].[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[C:15](=[O:31])[N:16]([CH:23]2[CH2:28][CH2:27][C:26](=[O:29])[NH:25][C:24]2=[O:30])[C:17]3=[O:22])=[C:8]([O:32][CH3:33])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58827272HCID 58827272, compound

Product 1

HCID 67229171HCID 67229171, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

4-[4-(2-Dimethylaminoethoxy)-2-methoxyphenylamino]-2-(2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione (0.45 g, 1.0 mmol) was dissolved in 9:1 methylene chloride-methanol (30 mL) and a 2 M solution of hydrogen chloride in ether (2.0 mL) was added. The mixture was stirred at room temperature for 1 hour, and was evaporated under vacuum. The residue was triturated with ether and filtered, providing 0.49 g, in quantitative yield: mp>260° C.; 1H NMR (DMSO-d6) δ 2.04-2.09 (m, 1H), 2.57-2.64 (m, 2H), 2.84-2.91 (m, 7H), 3.50 (t, J=4.6 Hz, 2H), 3.81 (s, 3H), 4.39 (t, J=4.6 Hz, 2H), 5.11 (dd, J=13.4 Hz, J=5.2 Hz, 1H), 6.65 (dd, J=8.6 Hz, J=2.0 Hz, 1H), 6.80 (d, J=2.0 Hz, 1H), 7.04 (d, J=8.4 Hz, 1H), 7.17 (d, J=7.0 Hz, 1H), 7.34 (d, J=8.6 Hz, 1H), 7.56 (t, J=7.8 Hz, 1H), 8.00 (s, 1H), 10.57 (br, 1H), 11.14 (s, 1H); 13C NMR (DMSO-d6) δ 22.1, 31.0, 42.7, 48.7, 55.2, 55.9, 62.7, 100.4, 105.7, 110.6, 112.4, 118.3, 121.1, 124.8, 132.1, 136.2, 144.0, 153.4, 155.9, 167.1, 168.8, 170.0, 172.8; Anal. calcd for C24H27ClN4O6.0.1Et2O.0.8H2O: C, 55.85; H, 5.69; N, 10.68. Found: C, 55.80; H, 5.32; N, 10.38.

Workup

  1. customwas evaporated under vacuum
  2. customThe residue was triturated with ether
  3. filtrationfiltered
  4. customproviding 0.49 g

Sources & evidence

ORD record
ord-6e042fbe5d0044878acb025f38333f11
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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