Hydrogen chloride-ethyl acetate → HCID 22492917, compound

HRID 1816319Notes

Reaction equation

HRID 1816319 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1.C(OC(=O)C)C.Cl>C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 22492895HCID 22492895, compound

Product 1

HCID 22492917HCID 22492917, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(5-methoxypentyloxy)-1-N-t-butoxycarbonylpiperidine (1.97 g) in ethyl acetate (20 ml) was added 4N-hydrogen chloride ethyl acetate solution (16.3 ml), and the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was evaporated in vacuo. The resulting residue was dissolved in a mixture of dichloromethane and methanol (10:1; 50 ml: 5 ml). To this solution was added 1N-sodium hydroxide (5 ml) with stirring. The organic layer was separated and evaporated under reduced pressure to give 4-(5-methoxypentyloxy)-piperidine (0.62 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionThe resulting residue was dissolved in a mixture of dichloromethane and methanol (10:1; 50 ml: 5 ml)
  3. additionTo this solution was added 1N-sodium hydroxide (5 ml)
  4. stirringwith stirring
  5. customThe organic layer was separated
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f9ccb9acc69d423ca1d953f5c4d172d1
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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