Acetic Acid → (2,2-Dimethoxy-ethyl)-(3-piperidin-1-yl-propyl)-amine

HRID 1096271Notes

Reaction equation

HRID 1096271 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][NH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH:14]=O.S([O-])([O-])(=O)=O.[Mg+2].CC(O)=O.C([BH3-])#N.[Na+]>CO>[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14][NH:10][CH2:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 19049Piperidine-1-propylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 5003444Sodium cyanoborohydride

Product 1

HCID 63685354(2,2-Dimethoxy-ethyl)-(3-piperidin-1-yl-propyl)-amineYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-piperidinepropylamine (3.00 g, 21.1 mmol) in MeOH (60 mL) were added dimethoxyacetaldehyde (45% solution in TBME, 6.5 mL, 25 mmol) magnesium sulfate (22.8 g, 190 mmol), AcOH (5.07 g, 84.4 mmol), and sodium cyanoborohydride (1.99 g, 31.6 mmol) at 0° C. The ice bath was removed, then after 18 h the reaction mixture was partitioned between sat. aq. sodium hyrogencarbonate solution and EtOAc. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2; CH2Cl2/MeOH/25% aq. ammonia solution 90:10:0.25) afforded the title compound (2.08 mg, 43%). Colorless liquid, 231.2 (M+H)+.

Workup

  1. customThe ice bath was removed
  2. customafter 18 h the reaction mixture was partitioned between sat. aq. sodium hyrogencarbonate solution and EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-6380dc38792e474d9851278c04ab709c
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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