Benzaldehyde → HCID 178519470, compound

HRID 1896987Notes

Reaction equation

HRID 1896987 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.[C:9]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=O)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:34]1([CH:40]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:41][N+:42]#[C-:43])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C[OH:51]>>[C:9]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([N:1]([CH:26]([C:43](=[O:51])[NH:42][CH2:41][CH:40]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:2][CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1)=[O:21])(=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 5

HCID 240BenzaldehydeHCID 887MethanolHCID 68132-Benzoylbenzoic AcidHCID 2758714HCID 2758714, compoundHCID 178419017HCID 178419017, compound

Product 1

HCID 178519470HCID 178519470, compoundYield 47%

Procedure

A solution of histamine (1.11 g, 10.0 mmol), 2-benzoylbenzoic acid (2.26 g, 10.0 mmol), benzaldehyde (1.06 g, 10.0 mmol) and the product of step 1 (2.07 g, 10.0 mmol) in methanol was heated at reflux overnight. The reaction was concentrated and the residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was dried (sodium sulfate) and concentrated to afford a foamy light brown solid. Flash chromatography over silica (methylene chloride/methanol) afforded 2.99 g (47%) of the product as a beige solid: 1H NMR (CDCl3) δ 7.88-6.84 (m, 25H), 6.65-6.25 (m, 2H), 5.66-5.30 (m, 1H), 4.44-4.20 (m, 1H), 4.17-3.84 (m, 2H), 3.47-3.03 (m, 2H), 2.69-2.18 (m, 2H) ppm. MS (ESI) m/z 634 (M+H+).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction was concentrated
  3. customthe residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. concentrationconcentrated
  6. customto afford a foamy light brown solid

Sources & evidence

ORD record
ord-4ca91a20ef634f6aa272682f9040f0e6
Source dataset
uspto-grants-2013_08
Patent number
US08518999B2

Reaction notes

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