Acetone → Tert-butyl 4-(iodomethyl)piperidine-1-carboxylate

HRID 1357913Notes

Reaction equation

HRID 1357913 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[I-:19].[Na+].[CH3:21]C(C)=O>>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][CH:6]([CH2:21][I:19])[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 10448961Tert-butyl 4-(iodomethyl)piperidine-1-carboxylate

Procedure

A mixture of 1-(t-butoxycarbonyl)piperidin-4-yl methanesulfonate (13.58 g, 46.4 mmol) and sodium iodide (34.68 g, 232 mmol) in acetone (80 mL) was heated to reflux for 3 h. The mixture was partitioned between ether (350 mL) and water (350 mL). The organic layer was washed with saturated aq. brine (250 mL), and the aqueous layers were extracted in succession with ether (250 mL). The combined organic layers were dried (sodium sulfate), decanted, and evaporated to give the title compound (14.8 g) as a pale yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customThe mixture was partitioned between ether (350 mL) and water (350 mL)
  4. washThe organic layer was washed with saturated aq. brine (250 mL)
  5. extractionthe aqueous layers were extracted in succession with ether (250 mL)
  6. dry with materialThe combined organic layers were dried (sodium sulfate)
  7. customdecanted
  8. customevaporated

Sources & evidence

ORD record
ord-dfb0d2ae378c430eab1e83f2f877d989
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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