Acetic Acid → Methyl 3-aminopiperidine-1-carboxylate

HRID 2212180Notes

Reaction equation

HRID 2212180 reaction equation
C(O)(=O)C.Cl.[CH3:6][O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([NH:16]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:11]1)=[O:9]>C(#N)C>[CH3:6][O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([NH2:16])[CH2:11]1)=[O:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 696524093-(Trityl-amino)-piperidine-1-carboxylic acid methyl ester

Product 1

HCID 22273098Methyl 3-aminopiperidine-1-carboxylateYield 95.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add acetic acid saturated with HCl(g) (100 mL, ˜3N in HCl) to 3-(trityl-amino)-piperidine-1-carboxylic acid methyl ester (6.51 g, 16.2 mmol). Stir the solution vigorously at room temperature for 2 hours. Concentrate the reaction, follow this by addition of acetonitrile and concentration to assist in the removal of acetic acid (×2). Partition the resulting material between 1N HCl and ethyl acetate, separate the layers, extract the organic layer with 1N HCl. Basify the combined aqueous layers with 5N sodium hydroxide, extract with 20% isopropanol/chloroform (×3). Dry the combined organic layers over magnesium sulfate and concentrate to give 2.45 g of the title compound as a white solid, 95% yield. 1H NMR: consistent with structure. MS (ion spray) 158 (M+).

Workup

  1. concentrationConcentrate
  2. customthe reaction
  3. customto assist in the removal of acetic acid (×2)
  4. customPartition the resulting material between 1N HCl and ethyl acetate
  5. customseparate the layers
  6. extractionextract the organic layer with 1N HCl
  7. extractionextract with 20% isopropanol/chloroform (×3)
  8. dry with materialDry the combined organic layers over magnesium sulfate
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-8d411f7d4713493f87e38178998d2b8d
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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