N,1-dimethylpyrrolidin-3-amine → HCID 86619600, compound

HRID 2236850Notes

Reaction equation

HRID 2236850 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][CH:25]1[CH2:29][N:28]([CH3:30])[CH2:27][CH2:26]1.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)[CH:25]1[CH2:26][CH2:27][N:28]([CH3:30])[CH2:29]1

Participants

7

Reactant 3

HCID 2758520N,1-dimethylpyrrolidin-3-amineHCID 5003444Sodium cyanoborohydrideHCID 86619598HCID 86619598, compound

Product 1

HCID 86619600HCID 86619600, compoundYield 101.6%

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 N,N′-dimethyl-3-aminopyrrolidine (0.15 g, 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-{[methyl-(1-methyl-pyrrolidin-3-yl)-amino]-methyl}-piperidin-1-yl)-phenyl]-carbamate as a foam (0.27 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-71c25c38e91b4ae29904c65522c371a8
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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