1,1-Dimethylethyl 4-[(1-cyclobutyl-4-piperidinyl)methyl]-1-piperidinecarboxylate → 1-Cyclobutyl-4-(4-piperidinylmethyl)piperidine

HRID 1869624Notes

Reaction equation

HRID 1869624 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([CH2:11][CH:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1>Cl.O1CCOCC1>[CH:1]1([N:5]2[CH2:6][CH2:7][CH:8]([CH2:11][CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH2:9][CH2:10]2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 688866201,1-Dimethylethyl 4-[(1-cyclobutyl-4-piperidinyl)methyl]-1-piperidinecarboxylate

Product 1

HCID 688867961-Cyclobutyl-4-(4-piperidinylmethyl)piperidine

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

1,1-Dimethylethyl 4-[(1-cyclobutyl-4-piperidinyl)methyl]-1-piperidinecarboxylate (may be prepared as described in Description 5) (5.7 g) was stirred in a solution of HCl-Dioxane (100 ml, 4M) for 1 h. The solvent was evaporated and the resultant yellow solid was dissolved in saturated potassium carbonate (25 ml). The solution was extracted into dichloromethane (3×50 ml) and the combined organics dried (MgSO4) and evaporated to give the title compound (D6) as a pale yellow oil which solidified on standing (3.04 g).

Workup

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

Sources & evidence

ORD record
ord-0209d218afad4217a0d6227676954daf
Source dataset
uspto-grants-2009_12
Patent number
US07638631B2

Reaction notes

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