Dichloromethane → HCID 68814146, compound

HRID 730029Notes

Reaction equation

HRID 730029 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([CH2:13][CH2:14][CH:15]=O)[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([CH:27]([NH2:29])[CH3:28])[C:26]2[C:20]([CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].C(Cl)[Cl:47]>>[ClH:47].[C:17]1([CH:27]([NH:29][CH2:15][CH2:14][CH2:13][C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:12]=2)[CH3:28])[C:26]2[C:20]([CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 57834058HCID 57834058, compoundHCID 57834130HCID 57834130, compound

Product 1

HCID 68814146HCID 68814146, compound

Procedure

Dehydrated methylene chloride (2 mL) was added with 3-(6-phenylpyridin-2-yl)propane aldehyde (52.5 mg), [1-(azulen-1-yl)ethyl]amine (63.3 mg), and sodium triacetoxyborohydride (158.9 mg, Aldrich), and stirred at room temperature for 72 hours. The reaction mixture was added with 2 N sodium hydroxide, and extracted with chloroform. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=15:1) to obtain 63.2 mg of the title compound in the free form. This compound was dissolved in chloroform, and added with 0.1 N solution of hydrochloric acid in methanol (1.7 mL), and the solvent was evaporated under reduced pressure to obtain 69.3 mg of the title compound.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-5f3b2c13c48e4b10acec27075031fc2f
Source dataset
uspto-grants-2009_09
Patent number
US07582658B2

Reaction notes

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