Sodium Carbonate → 3-(4-(Methylamino)piperidin-1-yl)-3-oxopropionic acid methyl ester hydrochloride

HRID 636965Notes

Reaction equation

HRID 636965 reaction equation
[ClH:1].CN.[CH3:4][O:5][C:6](=[O:17])[CH2:7][C:8](=[O:16])[N:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.[C:18]([BH3-])#[N:19].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[ClH:1].[CH3:4][O:5][C:6](=[O:17])[CH2:7][C:8]([N:9]1[CH2:14][CH2:13][CH:12]([NH:19][CH3:18])[CH2:11][CH2:10]1)=[O:16]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 544109143-Oxo-3-(4-oxopiperidin-1-yl)propionic acid methyl ester

Product 1

HCID 697805703-(4-(Methylamino)piperidin-1-yl)-3-oxopropionic acid methyl ester hydrochlorideYield 57.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of methylamine hydrochloride (67.5 g, 10 eq) in methanol (520 mL) was added a solution of 3-oxo-3-(4-oxopiperidin-1-yl)propionic acid methyl ester (20 g; 0.1 mol) in methanol (170 mL) and stepwise sodium cyanoborohydride (powder; 5.03 g, 0.08 mol). The reaction mixture was stirred 24 hours at room temperature. After addition of a saturated water solution of sodium carbonate, the residue was evaporated and extracted with dichloromethane. The organic phase was dried and evaporated to yield the crude 3-(4-(methylamino)piperidin-1-yl)-3-oxopropionic acid methyl ester (11.6 g) which was converted to the hydrochloride with hydrogen chloride in ethyl acetate/methanol.

Workup

  1. customthe residue was evaporated
  2. extractionextracted with dichloromethane
  3. customThe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-2c2a80f25c374fafb467146c34267872
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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