Piperidine → HCID 86717258, compound

HRID 1482767Notes

Reaction equation

HRID 1482767 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH2:11][C@@H:12]4[N:18]([CH:19]=3)[C:17](=[O:20])[C:16]3[CH:21]=[C:22]([O:83][CH3:84])[C:23]([O:25][CH2:26][CH2:27][CH2:28][O:29][C:30]5[C:80]([O:81][CH3:82])=[CH:79][C:33]6[C:34](=[O:78])[N:35]7[CH:41]=[C:40]([C:42]8[CH:47]=[CH:46][C:45]([NH:48][C:49](=[O:77])[C@@H:50]([NH:52][C:53](=[O:76])[C@@H:54]([NH:58]C(=O)OCC9C%10C=CC=CC=%10C%10C9=CC=CC=%10)[CH:55]([CH3:57])[CH3:56])[CH3:51])=[CH:44][CH:43]=8)[CH2:39][C@H:36]7[CH:37]=[N:38][C:32]=6[CH:31]=5)=[CH:24][C:15]=3[N:14]=[CH:13]4)=[CH:9][C:4]=2[O:3][CH2:2]1.N1CCCCC1>CN(C=O)C>[NH2:58][C@@H:54]([CH:55]([CH3:57])[CH3:56])[C:53]([NH:52][C@@H:50]([CH3:51])[C:49]([NH:48][C:45]1[CH:44]=[CH:43][C:42]([C:40]2[CH2:39][C@@H:36]3[N:35]([CH:41]=2)[C:34](=[O:78])[C:33]2[CH:79]=[C:80]([O:81][CH3:82])[C:30]([O:29][CH2:28][CH2:27][CH2:26][O:25][C:23]4[C:22]([O:83][CH3:84])=[CH:21][C:16]5[C:17](=[O:20])[N:18]6[CH:19]=[C:10]([C:8]7[CH:7]=[CH:6][C:5]8[O:1][CH2:2][O:3][C:4]=8[CH:9]=7)[CH2:11][C@H:12]6[CH:13]=[N:14][C:15]=5[CH:24]=4)=[CH:31][C:32]=2[N:38]=[CH:37]3)=[CH:47][CH:46]=1)=[O:77])=[O:76]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86717259HCID 86717259, compound

Product 1

HCID 86717258HCID 86717258, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The imine 35 (82 mg, 0.07 mmol, 1 equiv.) was dissolved in DMF (1 mL) before piperidine (0.2 mL, 2 mmol, excess) was added slowly. This solution was left to stir at room temperature for 20 minutes until LC/MS analysis showed complete consumption of starting material. The reaction mixture was diluted with CH2Cl2 (50 mL), washed with water (50 mL×4), dried with MgSO4, filtered and the solvent removed in vacuo. The product 33 was used without further purification in the next step. LC/MS (1.15 min (ES+) m/z (relative intensity) 910.60 ([M+H]+, 58).

Workup

  1. additionwas added slowly
  2. waitThis solution was left
  3. customconsumption of starting material
  4. additionThe reaction mixture was diluted with CH2Cl2 (50 mL)
  5. washwashed with water (50 mL×4)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe product 33 was used without further purification in the next step
  10. custom1.15 min (ES+) m/z (relative intensity) 910.60 ([M+H]+, 58)

Sources & evidence

ORD record
ord-9f0cb3ba07c447bbae35ab09b9a768f2
Source dataset
uspto-grants-2016_08
Patent number
US09415117B2

Reaction notes

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