N,N-Dimethylethylenediamine → HCID 86619597, compound

HRID 2236841Notes

Reaction equation

HRID 2236841 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)=O.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH2:27].C([BH3-])#N.[Na+]>CO.O.[Cl-].[Zn+2].[Cl-]>[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][NH:27][CH2:1][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 86619598HCID 86619598, compound

Product 1

HCID 86619597HCID 86619597, compoundYield 106.2%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of tert-butyl [4-(4-formyl-piperidin-1-yl)-phenyl]carbamate (0.30 g, 1.0 mmol) in methanol (5 mL) is added N,N-dimethylethylenediamine (0.18 g, 2.0 mmol). The reaction mixture is stirred for 10 minutes and then a mixture of zinc chloride (82 mg, 0.6 mmol) and sodium cyanoborohydride (75 mg, 1.2 mmol) in methanol (2 mL) is added in a dropwise fashion. After stirring for two hours at room temperature, the reaction mixture is diluted with water and extracted 3× with ethyl acetate. The combined extracts were washed once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give tert-butyl {4-[4-({[2-(dimethylamino)ethyl]amino}methyl)piperidin-1-yl]phenyl}carbamate as a white foam (0.4 g, 100%).

Workup

  1. additionis added in a dropwise fashion
  2. stirringAfter stirring for two hours at room temperature
  3. extractionextracted 3× with ethyl acetate
  4. washThe combined extracts were washed once with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02c03916c4454ddc974826f68934f9e7
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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