1,2-Dichloroethane → HCID 57908098, compound

HRID 1013088Notes

Reaction equation

HRID 1013088 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]([OH:13])=O.[NH:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C>[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]([N:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]1)=[O:13]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 337214-PiperidoneHCID 757711-HydroxybenzotriazoleHCID 179376112-Amino-1-benzothiophene-3-carboxylic acid

Product 1

HCID 57908098HCID 57908098, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-aminobenzo[b]thiophene-3-carboxylic acid (1.0 g, 1.0 equivalent) and 4-piperidone (1.0 equivalent) in DMF (0.33 M) was treated with EDC (1.0 equivalent), HOBt (1.0 equivalent) and Et3N (2.0 equivalents) at rt. The reaction mixture was stirred until the reaction was complete as determined by LCMS analysis and then partitioned between ethyl acetate and water. Organic layers were washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, and volatiles removed under reduced pressure. Residue was purified by SiO2 chromatography (5%-10% MeOH/CH2Cl2 gradient) to afford the 1-(2-aminobenzo[b]thiophene-3-carbonyl)piperidin-4-one (6A, 84%).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washOrganic layers were washed with saturated aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4, and volatiles
  4. customremoved under reduced pressure
  5. customResidue was purified by SiO2 chromatography (5%-10% MeOH/CH2Cl2 gradient)

Sources & evidence

ORD record
ord-65983179869a4c49adaa27fdc2c11737
Source dataset
uspto-grants-2011_07
Patent number
US07981904B2

Reaction notes

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