Acetic Acid → HCID 66638661, compound

HRID 1094998Notes

Reaction equation

HRID 1094998 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([CH:12]=O)[S:8][C:7]=1[NH:14][C:15](=[O:28])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH:17]=1)=[O:5])[CH3:2].[C:29](O)(=O)[CH3:30].C(O[BH-](O[C:43](=O)[CH3:44])OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[CH3:52][N:53](C)C=O>>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([CH2:12][N:53]2[CH2:30][CH2:29][CH2:44][CH2:43][CH2:52]2)[S:8][C:7]=1[NH:14][C:15](=[O:28])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]([CH2:24][CH3:25])[CH2:26][CH3:27])[CH:17]=1)=[O:5])[CH3:2]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86608145HCID 86608145, compound

Product 1

HCID 66638661HCID 66638661, compoundYield 64%

Procedure

2-(3-diethylaminomethyl-benzoylamino)-5-formyl-4-methyl-thiophene-3-carboxylic acid ethyl ester (110 mg) synthesized by the above process was dissolved in N,N-dimethylformamide (10 ml), acetic acid (100 μl) and sodium triacetoxyborohydride (66 mg) were added to the solution at room temperature, and the mixture was stirred at that temperature for one hr. After the completion of the reaction, the reaction solution was neutralized with a saturated sodium hydrogencarbonate solution, and was then subjected to separatory extraction with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-(3-diethylaminomethyl-benzoylamino)-4-methyl-5-piperidin-1-ylmethylthiophene-3-carboxylic acid ethyl ester (79 mg, yield 64%).

Workup

  1. customAfter the completion of the reaction
  2. extractionwas then subjected to separatory extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialwas dried over sodium sulfate
  5. concentrationwas then concentrated under the reduced pressure
  6. customThe residue was purified by column chromatography
  7. washeluted with a chloroform-methanol system

Sources & evidence

ORD record
ord-e67e0901493b45c1acaee5512717bcc3
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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