Water → 2-(2-benzofuranylmethyl)Piperidine

HRID 598536Notes

Reaction equation

HRID 598536 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1C(OC(C)(C)C)=O)=O.O.NN.[OH-].[K+].O>C(O)COCCO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 23146395(RS)-2-(2-Benzofuranylcarbonyl)-1-(tert-butyloxycarbonyl)piperidine

Product 1

HCID 231462452-(2-benzofuranylmethyl)PiperidineYield 36%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

To a solution of (RS)-2-(2-benzofuranylcarbonyl)-1-(tert-butyloxycarbonyl)piperidine (0.30 g, 0.91 mmol) in diethylene glycol (20 g), was added hydrazine hydrate (0.16 ml, 2.79 mmol) and the resultant mixture heated at 170° C. for 30 min. then cooled to room temperature. Potassium hydroxide (0.44 g, 7.86 mmol) was added and the mixture heated at 200° C. for 18 h. The resultant was then poured into water (100 ml) and extracted with diethyl ether (3×20 ml). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give the title compound (10 mg, 36%) as a golden oil.

Workup

  1. temperaturethe mixture heated at 200° C. for 18 h
  2. extractionextracted with diethyl ether (3×20 ml)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-f0d98b403b9847a3b5aeb14c41d58e0d
Source dataset
uspto-grants-2011_03
Patent number
US07897618B2

Reaction notes

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