1,2-Dichloroethane → (2-Methyl-piperidin-1-yl)-(5-phenyl-thiophen-3-yl)-methanone

HRID 1914546Notes

Reaction equation

HRID 1914546 reaction equation
[C:1]1([C:7]2[S:11][CH:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.[CH3:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]1.O>C(Cl)Cl>[CH3:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][N:21]1[C:12]([C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[S:11][CH:10]=1)=[O:14]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 79742-MethylpiperidineHCID 162272215-Phenylthiophene-3-carboxylic acid

Product 1

HCID 44224885(2-Methyl-piperidin-1-yl)-(5-phenyl-thiophen-3-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-phenyl-thiophene-3-carboxylic acid (1 eq.) in DCM (1 mL/100 mg SM) was added EDC (1.5 eq.). This mixture was stirred at room temperature for 5 minutes and then 2-methyl piperidine (1.2 eq.) was added and the mixture stirred for 18 hours. Water (1 mL/100 mg SM) was then added and the organic layer separated, dried and evaporated to give the crude product which was purified by column chromatography (EtOAc/iso-hexane). LCMS m/z 286 [M+H]+ R.T.=3.85 min (Analytical Method 3).

Workup

  1. stirringthe mixture stirred for 18 hours
  2. customthe organic layer separated
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-3499b28181c3482489c40d98ed6063dc
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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