4-Formylbenzoic acid → 4-{[4-(Morpholin-4-yl)anilino]methyl}benzoic acid

HRID 252778Notes

Reaction equation

HRID 252778 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=O.[O:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1.[Sn](CCCC)(CCCC)(Cl)Cl.C1([SiH3])C=CC=CC=1>C1COCC1>[N:15]1([C:18]2[CH:19]=[CH:20][C:21]([NH:22][CH2:1][C:3]3[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=3)=[CH:23][CH:24]=2)[CH2:14][CH2:13][O:12][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 120884-Formylbenzoic acidHCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 75655Benzenamine, 4-(4-morpholinyl)-

Product 1

HCID 224786714-{[4-(Morpholin-4-yl)anilino]methyl}benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-formylbenzoic acid (2.53 g; 16.8 mmol; 1 eq), 4-morpholinoaniline (3 g; 16.8 mmol; 1 eq) and Bu2SnCl2 (510 mg; 1.68 mmol; 0.1 eq) in dry THF (20 ml) was treated with PhSiH3 (3.31 ml; 16.8 mmol; 1 eq) at room temperature for 12 h. The reaction, was filtered and the solid product was washed with MeOH. The yield of the reaction was 5.25 g (99%). LRMS: calc 312.37. found: 313.2.

Workup

  1. customThe reaction
  2. filtrationwas filtered
  3. washthe solid product was washed with MeOH

Sources & evidence

ORD record
ord-6d838fb079024bf49f8ebf0e0a96b6a4
Source dataset
uspto-grants-2011_01
Patent number
US07868204B2

Reaction notes

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