Piperazine → HCID 21073348, compound

HRID 1373654Notes

Reaction equation

HRID 1373654 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][C:10](=[O:12])[NH:9][C:8]2[N:7]=[C:6]([O:13][CH2:14][CH2:15][CH2:16][CH:17]=O)[CH:5]=[CH:4][C:3]1=2.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(O[BH-](O[C:36](=O)[CH3:37])OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:19])[C:3]2[C:8](=[N:7][C:6]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][N:20]3[CH2:25][CH2:24][N:23]([C:1]4[CH:2]=[CH:3][CH:8]=[C:37]5[C:36]=4[N:7]=[CH:6][CH:5]=[CH:4]5)[CH2:22][CH2:21]3)=[CH:5][CH:4]=2)[NH:9][C:10](=[O:12])[CH2:11]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 21073353HCID 21073353, compound

Product 1

HCID 21073348HCID 21073348, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The aldehyde (0.3 mmol) and the piperazine (60.306 mmol) were combined in methylene chloride and stirred in a vial over sieves for 10 min. Sodium triacetoxyborohydride (0.42 mmol) was added and the reaction was stirred overnight. The reaction was quenched by slowly adding water and then the mixture was filtered. The residue was partitioned between CH2Cl2 and water and the organic layer was concentrated. Purification by liquid chromatography (MPLC, gradient of 100% CH2Cl2 to 100% of a 10% MeOH in CH2Cl2 solution) gave the title compound. The final products were made into hydrochloride salts by treatment with a solution of saturated HCl in MeOH.

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe reaction was quenched by slowly adding water
  3. filtrationthe mixture was filtered
  4. customThe residue was partitioned between CH2Cl2 and water
  5. concentrationthe organic layer was concentrated
  6. customPurification by liquid chromatography (MPLC, gradient of 100% CH2Cl2 to 100% of a 10% MeOH in CH2Cl2 solution)

Sources & evidence

ORD record
ord-ebafe291aba64af9b8db5467284e5716
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

Loading…