Dimethylamine → HCID 86619599, compound

HRID 2236849Notes

Reaction equation

HRID 2236849 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][NH:24][CH3:25].C([BH3-])#N.[Na+]>CO.O.[Cl-].[Zn+2].[Cl-]>[CH3:23][N:24]([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)[CH3:25]

Participants

7

Reactant 3

HCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 86619598HCID 86619598, compound

Product 1

HCID 86619599HCID 86619599, compoundYield 149.9%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of tert-butyl [4-(4-formyl-piperidin-1-yl)-phenyl]carbamate (0.20 g, 0.66 mmol) in methanol (5 mL) is added dimethylamine (2.0 M solution in tetrahydrofuran, 0.66 mL, 1.3 mmol). The reaction mixture is stirred for 20 minutes and then a mixture of zinc chloride (53 mg) and sodium cyanoborohydride (50 mg) in methanol (2 mL) is added in a dropwise fashion. After stirring overnight 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-dimethylaminomethyl-piperidin-1-yl)-phenyl]-carbamate as a white foam (0.33 g, >100%).

Workup

  1. additionis added in a dropwise fashion
  2. stirringAfter stirring overnight 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-aa46e98bf52c4523a022d4850666f68b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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