1,1-Dimethylethyl 4-[(1-ethyl-4-piperidinyl)methyl]-1-piperidinecarboxylate → 1-Ethyl-4-(piperidin-4-ylmethyl)piperidine

HRID 1869626Notes

Reaction equation

HRID 1869626 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[CH2:5][CH2:4]1)[CH3:2]>Cl.O1CCOCC1>[CH2:1]([N:3]1[CH2:4][CH2:5][CH:6]([CH2:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:7][CH2:8]1)[CH3:2]

Participants

3

Reactant 1

HCID 688869521,1-Dimethylethyl 4-[(1-ethyl-4-piperidinyl)methyl]-1-piperidinecarboxylate

Product 1

HCID 534072191-Ethyl-4-(piperidin-4-ylmethyl)piperidineYield 87.4%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

1,1-Dimethylethyl 4-[(1-ethyl-4-piperidinyl)methyl]-1-piperidinecarboxylate (may be prepared as described in Description 7) (2.5 g) was stirred in a solution of HCl-Dioxane (70 ml, 4M) for 2 h. The solvent was evaporated and the resultant hydrochloride salt was dissolved in saturated potassium carbonate (25 ml). The solution was extracted into DCM (3×50 ml) and the combined organics dried (MgSO4) and evaporated to give the title compound (D8) (1.48 g).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resultant hydrochloride salt was dissolved in saturated potassium carbonate (25 ml)
  3. extractionThe solution was extracted into DCM (3×50 ml)
  4. dry with materialthe combined organics dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-5f11804044cf414b8dd5924d975cae79
Source dataset
uspto-grants-2009_12
Patent number
US07638631B2

Reaction notes

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