Acetic Acid → 1-(4-(4-((Cyclobutylamino)methyl)phenyl)piperazin-1-yl)ethanone

HRID 1505609Notes

Reaction equation

HRID 1505609 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH:18]1([NH2:22])[CH2:21][CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[CH:18]1([NH:22][CH2:14][C:13]2[CH:16]=[CH:17][C:10]([N:7]3[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]3)=[CH:11][CH:12]=2)[CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 75645CyclobutylamineHCID 20521464-(4-Acetylpiperazin-1-yl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 866906431-(4-(4-((Cyclobutylamino)methyl)phenyl)piperazin-1-yl)ethanoneYield 100.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 4-(4-acetylpiperazin-1-yl)benzaldehyde (150 mg, 0.64 mmol) and cyclobutylamine (75 mg, 0.77 mmol) in dichloroethane (1.5 mL) was added sodium triacetoxyborohydride (216 mg, 0.96 mmol), followed by acetic acid (0.055 mL, 0.96 mmol) and the reaction was stirred at ambient temperature for 16 hours. The reaction was then quenched with 1 N aqueous NaOH, diluted with dichloromethane and the dichloromethane layer was isolated with a phase-separator cartridge and concentrated to give 1-(4-(4-((cyclobutylamino)methyl)phenyl)piperazin-1-yl)ethanone (185 mg). The product was used without purification. LCMS (m/z) ES+ 288 [M+1]+.

Workup

  1. customThe reaction was then quenched with 1 N aqueous NaOH
  2. additiondiluted with dichloromethane
  3. customthe dichloromethane layer was isolated with a phase-separator cartridge
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ef63b15ff3904cf69264c4e7781df821
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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