Hydrochloric Acid → HCID 67835394, compound

HRID 1493422Notes

Reaction equation

[OH:1][C:2]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH2:17]([N:21]([CH:26]1[CH2:31][C:30]([CH3:33])([CH3:32])[N:29]([O:34][CH3:35])[C:28]([CH3:37])([CH3:36])[CH2:27]1)[C:22](=[O:25])[CH2:23]Cl)[CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>C(OCC)(=O)C.CN(C)C=O>[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH2:23][C:22]([N:21]([CH:26]2[CH2:31][C:30]([CH3:33])([CH3:32])[N:29]([O:34][CH3:35])[C:28]([CH3:36])([CH3:37])[CH2:27]2)[CH2:17][CH2:18][CH2:19][CH3:20])=[O:25])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 10.1 g (47.0 mmol) of 2,4-dihydroxybenzophenone, 15.0 g (47.0 mmol) of N-butyl-N-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)chloroacetamide, 19.5 g (0.141 mol) of potassium carbonate, 0.8 g (4.7 mmol) of potassium iodide, and 100 ml of N,N-dimethylformamide is heated at 80° C. for 20 hours. The reaction mixture is treated with 1N hydrochloric acid (600 ml). The brown precipitate is dissolved in ethyl acetate (400 ml), and this solution is washed with water (200 ml) and saturated sodium chloride solution (200 ml), then dried over magnesium sulfate and concentrated to a glass. Purification by flash chromatography on silica gel (3:1 heptane: ethyl acetate) affords 5.4 g (23% yield) of the title compound, a yellow glass.

Workup

washthis solution is washed with water (200 ml) and saturated sodium chloride solution (200 ml)
dry with materialdried over magnesium sulfate
concentrationconcentrated to a glass
customPurification by flash chromatography on silica gel (3:1 heptane: ethyl acetate)

Sources & evidence

ORD record: ord-32be0f18655445a19716d6f6dcea8358
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05021478

Reaction notes

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