Piperidine → 2-[3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-N-[2-(4-piperidin-1-ylmethyl-phenyl)-ethyl]-acetamide

HRID 1444722Notes

Reaction equation

HRID 1444722 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12](=[O:31])[CH2:13][CH:14]2[C:19](=[O:20])[NH:18][CH:17]=[CH:16][N:15]2[S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:5][CH:4]=1.[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>C(Cl)Cl>[O:20]=[C:19]1[NH:18][CH:17]=[CH:16][N:15]([S:21]([C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)(=[O:23])=[O:22])[CH:14]1[CH2:13][C:12]([NH:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:4][CH:5]=1)=[O:31]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 68682701N-[2-(4-chloromethyl-phenyl)-ethyl]-2-[3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-acetamide

Product 1

HCID 686782362-[3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-N-[2-(4-piperidin-1-ylmethyl-phenyl)-ethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-[2-(4-chloromethyl-phenyl)-ethyl]-2-[3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-acetamide (195 mg, 0.42 mmol) in CH2Cl2 (2 mL) was added piperidine (Aldrich, 0.13 mL, 1.3 mmol) at rt. The reaction mixture was stirred at rt overnight and then diluted with CH2Cl2 (50 mL). The organic solution was washed with saturated NaHCO3, and brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by preparative TLC (7% MeOH—CH2Cl2) afforded the title compound. MS (ESI): 511 (M+H)+.

Workup

  1. washThe organic solution was washed with saturated NaHCO3, and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by preparative TLC (7% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-6fd74f8e79b547488ba515ab440634a5
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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