2-Mercaptoethanol → HCID 66747303, compound

HRID 1422769Notes

Reaction equation

HRID 1422769 reaction equation
N12CCCN=C1CCCCC2.[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([N:18]=[CH:19][C:20]([S:24][CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][CH:30]([N:33]([CH3:46])S(C4C=CC=CC=4[N+]([O-])=O)(=O)=O)[CH2:29][CH2:28]3)=[N:21]2)=[CH:16][CH:15]=1.SCCO>CN(C)C=O>[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([N:18]=[CH:19][C:20]([S:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][CH:30]([NH:33][CH3:46])[CH2:31][CH2:32]3)=[N:21]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66746540HCID 66746540, compound

Product 1

HCID 66747303HCID 66747303, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,8-diazabicyclo[5.4.0]undec-7-ene (36 μL, 0.24 mmol, 1.2 eq) is added at room temperature to a stirred solution of N-{1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-N-methyl-2-nitro-benzenesulfonamide (104 mg, 0.20 mmol, 1.0 eq) in N,N-dimethylformamide (3 mL), followed by 2-mercaptoethanol (56 μL, 0.90 mmol, 1.5 eq). After 15 hours stirring at room temperature, solvent is evaporated and the residue is extracted with ethyl acetate (3×10 mL) and water (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford {1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidin-4-yl}-methyl-amine as a yellow oil (43 mg, 62% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with ethyl acetate (3×10 mL) and water (10 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bb0a3282fe03410bba3a938d8b86590e
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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