Hydrochloric Acid → 4-(3,4-Dichlorophenoxy)-1-piperidinepropanamine

HRID 915543Notes

Reaction equation

HRID 915543 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][NH:15]C(=O)OC(C)(C)C)[CH2:8][CH2:7]1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[Cl:26])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][NH2:15])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11188863Tert-butyl 3-[4-(3,4-dichlorophenoxy)-1-piperidinyl]propylcarbamate

Product 1

HCID 113241264-(3,4-Dichlorophenoxy)-1-piperidinepropanamineYield 73.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The product from Step (a) (2 g) was dissolved in dioxane (100 ml) and 6N HCl (100 ml) was added. After 18 hours at room temperature the solvent was evaporated and the resultant solid was dissolved in aqueous NaOH (2M) to pH 11. The solution was extracted with ethyl acetate, the organic phase was dried (MgSO4) and evaporated to leave the title compound as an oil (1.1 g).

Workup

  1. customAfter 18 hours at room temperature the solvent was evaporated
  2. dissolutionthe resultant solid was dissolved in aqueous NaOH (2M) to pH 11
  3. extractionThe solution was extracted with ethyl acetate
  4. dry with materialthe organic phase was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-5804d3a6f85b4ba48421d1f3a3abacda
Source dataset
uspto-grants-2007_09
Patent number
US07265227B2

Reaction notes

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