Water → HCID 10110588, compound

HRID 989273Notes

Reaction equation

HRID 989273 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.Cl[CH2:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22].O>CO>[CH3:22][N:21]([CH3:23])[CH2:20][CH2:19][CH2:18][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 691504,4'-Dihydroxybenzophenone

Product 1

HCID 10110588HCID 10110588, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of bis-(4-hydroxy-phenyl)-methanone (7.00 g) in methanol (130 mL) was added at room temperature t-Bu3OK (14.7 g) followed by (3-chloro-propyl)-dimethyl-amine (10.3 g). The reaction mixture was heated under reflux for 18 h and was allowed to cool down to room temperature. Water (50 mL) was added and the solvent was removed in vacuo. Methylene chloride (650 mL) was added and the organic layer was washed with water (2×150 mL). The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo. The crude products were separated and purified by flash chromatography on silica gel (chloroform/2 M ammonia in methanol) to give the title compound bis-[4-(3-dimethylamino-propoxy)-phenyl]-methanone as a colorless residue (250 mg). 1H NMR (400 MHz, CD3OD): 7.78 (d, 4 H), 7.09 (d, 4 H), 4.22 (t, 4 H), 3.37-3.40 (m, 4 H), 2.96 (s, 12 H), 2.24-2.31 (m, 4 H). And title compound [4-(3-dimethylamino-propoxy)-phenyl]-(4-hydroxy-phenyl)-methanone as a colorless residue (150 mg). 1H NMR (400 MHz, CD3OD): 7.88-7.99 (m, 4 H), 7.25-7.29 (m, 2 H), 7.08-7.13 (m, 2 h), 4.48 (t, 2 H), 2.69-2.76 (m, 2 H), 2.56 (s, 6 H), 2.23-2.30 (m, 2 H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 h
  3. customthe solvent was removed in vacuo
  4. additionMethylene chloride (650 mL) was added
  5. washthe organic layer was washed with water (2×150 mL)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customThe crude products were separated
  9. custompurified by flash chromatography on silica gel (chloroform/2 M ammonia in methanol)

Sources & evidence

ORD record
ord-651efaa9736f4758b06b79b6a3bf4fbd
Source dataset
uspto-grants-2003_10
Patent number
US06638967B2

Reaction notes

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