Bromocyclopentane → 1-Cyclopentylpiperidin-4-ol

HRID 272845Notes

Reaction equation

HRID 272845 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[CH:14]1(Br)[CH2:18][CH2:17][CH2:16][CH2:15]1>CO>[CH:14]1([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 79341Piperidin-4-ol

Product 1

HCID 217027851-Cyclopentylpiperidin-4-olYield 71.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Hydroxypiperidine (2.08 g, 21.2 mmol), K2CO3 (5.86 g, 2 eq.), cylopentylbromide (11.51 g, 77.6 mmol, 3.7 eq.) and MeOH (20.8 ml) were refluxed together overnight. The reaction was allowed to cool to room temperature and quenched with 2M HCl solution (40 ml) and extracted with TBME (40 ml). The aqueous phase was basified to pH 14 with a 2M NaOH solution and extracted with DCM (4×50 ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give 1-cyclopentyl-4-hydroxypiperidine (2.55 g, 71%) as a pale yellow oil.

Workup

  1. customquenched with 2M HCl solution (40 ml)
  2. extractionextracted with TBME (40 ml)
  3. extractionextracted with DCM (4×50 ml)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. washwashed with DCM
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc9458b8f94b44a59a393f9bdb1cd505
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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