2-Bromopropane → 1-Isopropylpiperidin-4-ol

HRID 272842Notes

Reaction equation

HRID 272842 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH:15]([CH3:17])[CH3:16]>CO>[CH:15]([N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 79341Piperidin-4-ol

Product 1

HCID 796811-Isopropylpiperidin-4-olYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Hydroxypiperidine (2.13 g, 21.1 mmol), K2CO3 (5.83 g, 2 eq.), 2-bromopropane (11.2 g, 91 mmol, 4.3 eq.) and MeOH (21.3 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 2M NaOH solution and extracted with DCM (9×50 ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give 1-isopropyl-4-hydroxypiperidine (2.41 g, 80%) as a pale yellow oil.

Workup

  1. customquenched with 2M HCl solution (40 ml)
  2. extractionextracted with TBME (40 ml)
  3. extractionextracted with DCM (9×50 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-b0b76fbc78e1415187f5e84fbb8f54b7
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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