1-Methylpiperazine → HCID 86685998, compound

HRID 2277704Notes

Reaction equation

HRID 2277704 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:26])[N:21]([C:27]1[C:28]([CH:33]=O)=[CH:29][CH:30]=[N:31][CH:32]=1)[CH2:20][CH2:19]2.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>C(Cl)Cl.CO>[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:26])[N:21]([C:27]1[CH:32]=[N:31][CH:30]=[CH:29][C:28]=1[CH2:33][N:39]1[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]1)[CH2:20][CH2:19]2

Participants

6

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86685999HCID 86685999, compound

Product 1

HCID 86685998HCID 86685998, compoundYield 19.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

NaBH(OAc)3 (84 mg, 0.4 mmol) was added into a solution of 5-(6-chloro-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-pyridine-4-carbaldehyde (28.6 mg, 0.1 mmol) and 1-methyl-piperazine (10 mg 0.1 mmol) in DCM and MeOH (10 mL, 1:1). The reaction mixture was stirred at RT overnight before it was poured into ice-water (10 mL) and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried over anhy. MgSO4, filtered and concentrated in vacuo to give a crude product which was then purified by prep-HPLC to give title compound (7.2 mg, 16%) as a white solid. MS: 371.1 (M+H+).

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe organic layers were washed with brine
  3. customdried over anhy
  4. filtrationMgSO4, filtered
  5. concentrationconcentrated in vacuo
  6. customto give a crude product which
  7. customwas then purified by prep-HPLC

Sources & evidence

ORD record
ord-95c152be93294818a02370db680ebab1
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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