1,4-Dioxane → HCID 69425422, compound

HRID 1352490Notes

Reaction equation

HRID 1352490 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:14]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:13][C@@H:12]1[CH3:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[O:39]1CCO[CH2:41][CH2:40]1>>[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:14]([N:21]([C:40](=[O:39])[CH3:41])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:13][C@@H:12]1[CH3:29])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 69429086HCID 69429086, compound

Product 1

HCID 69425422HCID 69425422, compound

Procedure

To a solution of Cis-2-Methyl-4-benzylamino-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (300 mg, 0.776 mmol), diisopropyl ethyl amine (0.135 mL, 0.776 mmol) in dioxane (1.5 mL), was added anhydride acetic (0.732 mL, 7.76 mmol) with stirring. The mixture was heated under reflux over night, cooled and directly chromatographed on silica gel utilizing 50% ethyl acetate/hexane to provide the title compound (300 mg) as an oil. 1H NMR [CDCl3]: δ 7.6–6.9 (m, 14H), 5.5 (d, 1H), 5.3 (d, 1H), 5.2 (t, 1H), 4.8 (m, 1H), 4.4 (m, 2H), 3.8 (d, 1H), 2.4 (s, 3H), 1.5 (m, 1H), 1.2 (m, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux over night
  3. temperaturecooled
  4. customdirectly chromatographed on silica gel utilizing 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b8e32d7b7c074ca292dc6634591c788c
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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