1,1-Dimethylethyl 4-{[1-(cyclopropylmethyl)-4-piperidinyl]methyl}-1-piperidinecarboxylate → 1-(Cyclopropylmethyl)-4-(4-piperidinylmethyl)piperidine

HRID 1869628Notes

Reaction equation

HRID 1869628 reaction equation
[CH:1]1([CH2:4][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)[CH2:3][CH2:2]1>Cl.O1CCOCC1>[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][CH:8]([CH2:11][CH:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[CH2:7][CH2:6]2)[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 688855731,1-Dimethylethyl 4-{[1-(cyclopropylmethyl)-4-piperidinyl]methyl}-1-piperidinecarboxylate

Product 1

HCID 688844871-(Cyclopropylmethyl)-4-(4-piperidinylmethyl)piperidineYield 71.2%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

1,1-Dimethylethyl 4-{[1-(cyclopropylmethyl)-4-piperidinyl]methyl}-1-piperidinecarboxylate (may be prepared as described in Description 9) (2.0 g) was stirred in a solution of HCl-Dioxane (700 ml, 4M) for 2 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 (D10) (1.0 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-d559086f863143e38ba2ee3ddb87f8ba
Source dataset
uspto-grants-2009_12
Patent number
US07638631B2

Reaction notes

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