Benzaldehyde → HCID 178519470, compound

HRID 1410371Notes

Reaction equation

HRID 1410371 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-00ee53f294c14306ae767849d76dcb61
Source dataset
uspto-grants-2014_12
Patent number
US08921547B2

Reaction notes

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