1-((1-Methyl-4-piperidinyl)methyl)piperazine → Ammonia

HRID 469088Notes

Reaction equation

HRID 469088 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][C:19]([C:21]([O:23]CC)=O)=[N:18][N:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:26])[CH:4]=1.[CH3:27][N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH2:30][CH2:29]1>ClCCCl>[NH3:13].[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH3:14])[CH2:15][C:16]2[O:20][C:19]([C:21]([N:38]3[CH2:37][CH2:36][N:35]([CH2:34][CH:31]4[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]4)[CH2:40][CH2:39]3)=[O:23])=[N:18][N:17]=2)(=[O:12])=[O:11])=[C:5]([CH3:26])[CH:4]=1

Participants

5

Reactant 2

HCID 27369421-((1-Methyl-4-piperidinyl)methyl)piperazineHCID 58393140HCID 58393140, compound

Product 2

HCID 222AmmoniaHCID 46176410HCID 46176410, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate (1.0 g, 2.6 mmol) and 1-[(1-methylpiperidin-4-yl)methyl]piperazine (1.03 g, 5.2 mmol) were dissolved in DCE (5 mL) and stirred at 0° C. prior to degassing with N2. Trimethylaluminium (2M in toluene, 2.6 mL) was added dropwise to this solution. Upon complete addition, the reaction was stirred for 1 h at 80° C. The reaction was cooled, diluted with DCM (30 mL) and washed with saturated aqueous NaHCO3 (30 mL). The aqueous layer was extracted with DCM (2×30 mL) and the combined organic extracts dried over MgSO4 and concentrated in vacuo. The resulting brown oil was purified by FCC, eluting with 98:2 DCM:7N NH3 in MeOH to afford the title compound.

Workup

  1. customto degassing with N2
  2. additionTrimethylaluminium (2M in toluene, 2.6 mL) was added dropwise to this solution
  3. additionUpon complete addition
  4. stirringthe reaction was stirred for 1 h at 80° C
  5. temperatureThe reaction was cooled
  6. additiondiluted with DCM (30 mL)
  7. washwashed with saturated aqueous NaHCO3 (30 mL)
  8. extractionThe aqueous layer was extracted with DCM (2×30 mL)
  9. dry with materialthe combined organic extracts dried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customThe resulting brown oil was purified by FCC
  12. washeluting with 98:2 DCM

Sources & evidence

ORD record
ord-68296b61db154d0e9f99a43dd7bf265f
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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