Piperidine → Ammonia

HRID 1829178Notes

Reaction equation

HRID 1829178 reaction equation
[NH:1]1CCCC[CH2:2]1.I[CH:8]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]1.[C:19](=[O:22])([O-])[O-].[K+].[K+].C[N:26]1[CH2:30][CH2:29][CH2:28][C:27]1=O>>[NH3:1].[OH:22][C:19]1([CH3:2])[CH2:29][CH2:30][N:26]([CH:8]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylate

Product 2

HCID 222AmmoniaHCID 22061396HCID 22061396, compound

Conditions

Temperature
80 °C

Procedure

A mixture of the piperidine from preparation 26 (220 mg, 1.91 mmol), tert-butyl 3-iodo-1-azetidinecarboxylate (600 mg, 2.0 mmol) (EP 992493) and potassium carbonate (276 mg, 2.0 mmol) in 1-methyl-2-pyrrolidinone (10 ml) was stirred at 80° C. for 48 hours. The mixture was partitioned between water and ethyl acetate, and the layers separated. The organic phase was washed with water, then brine, dried (Na2SO4), and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (100:0:0 to 90:10:0.5) to afford the title compound, 162 mg.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. customthe layers separated
  3. washThe organic phase was washed with water
  4. dry with materialbrine, dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-0319bc5ac6dc4d409c1dc9aab191b572
Source dataset
uspto-grants-2006_06
Patent number
US07060836B2

Reaction notes

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