Piperidin-4-ol → 1-(Cyclopropylmethyl)piperidin-4-ol

HRID 1821982

Reaction equation

HRID 1821982 reaction equation
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[OH:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1>C1COCC1.C(OC(=O)C)C>[CH:5]1([CH2:4][N:10]2[CH2:11][CH2:12][CH:7]([OH:6])[CH2:8][CH2:9]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 79341Piperidin-4-olHCID 81503Bromomethylcyclopropane

Product 1

HCID 214287521-(Cyclopropylmethyl)piperidin-4-olYield 47%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add bromomethylcyclopropane (2.025 g, 15 mmol) to a solution of 4-hydroxypiperidine (3.035 g, 30 mmol) in THF (10 mL) and stir the mixture overnight. Dilute the mixture with ethylacetate, wash with saturated NaHCO3 solution, dry over Na2SO4, filter and concentrate to give a residue. Chromatography (silica gel, eluting with 8% 2M NH3-methanol in CH2Cl2) provides 1.087 g (47%) of the title compound: mass spectrum (ion spray): m/z=156.2 (M+1); 1H NMR (CDCl3, ppm): 3.60 (m, 1H), 2.81 (m, 2H), 2.16 (d, 1H), 2.10 (m, 3H), 1.84 (m, 2H), 1.53 (m, 3H), 0.79 (m, 1H), 0.44 (m, 2H), 0.00 (m, 2H).

Workup

  1. washwash with saturated NaHCO3 solution
  2. dry with materialdry over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. customto give a residue
  6. washChromatography (silica gel, eluting with 8% 2M NH3-methanol in CH2Cl2)

Sources & evidence

ORD record
ord-477683910d6f4a09a72aa1c87f311dca
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Linked notes

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