1-Methylpiperazine → HCID 66799339, compound

HRID 1193313Notes

Reaction equation

HRID 1193313 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][C:9]1([CH3:27])[CH2:14][C:13](=O)[CH2:12][CH2:11][CH:10]1[NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[CH3:8][C:9]1([CH3:27])[CH2:14][CH:13]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH2:12][CH2:11][CH:10]1[NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 66799079HCID 66799079, compound

Product 1

HCID 66799339HCID 66799339, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Methylpiperazine (0.620 ml, 5.6 mmol, 2 eq) was added at 0° C. to a solution of benzyl 2,2-dimethyl-4-oxocyclohexylcarbamate (770 mg, 2.8 mmol, 1 eq) in dichloromethane (15 ml), and stirring was carried out for 2 h at RT. Na(OAc)3BH (1.78 g, 8.4 mmol, 3 eq) was added in portions at 0° C., and stirring was carried out for 18 h at RT. The reaction solution was diluted with dichloromethane (60 ml), washed with water (50 ml) and sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated under reduced pressure. After purification by column chromatography (Alox neutral, 1% MeOH in dichloromethane), a white solid was obtained. Yield: 44% (440 mg, 1.225 mmol).

Workup

  1. stirringstirring
  2. waitwas carried out for 18 h at RT
  3. washwashed with water (50 ml) and sat. NaCl solution (50 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customAfter purification by column chromatography (Alox neutral, 1% MeOH in dichloromethane)
  7. customa white solid was obtained

Sources & evidence

ORD record
ord-704daf7e77534003aac7455e72f97e4f
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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