Cyclopentanone → 13-aza-6-oxadispiro[4.2.4.I]tridecane

HRID 276261Notes

Reaction equation

HRID 276261 reaction equation
[OH:1][CH2:2][C:3]1([NH2:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:9]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10]1>C1(C)C=CC=CC=1>[CH2:7]1[C:3]2([CH2:2][O:1][C:9]3([CH2:13][CH2:12][CH2:11][CH2:10]3)[NH:8]2)[CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 8452CyclopentanoneHCID 663071-Aminocyclopentanemethanol

Product 1

HCID 1831628713-aza-6-oxadispiro[4.2.4.I]tridecaneYield 175.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-hydroxymethylcyclopentanamine (Method B1c; 263 g, 2.3 mol) and cyclopentanone (220 mL, 1.3 mol, 1.1 equiv.) in toluene (2.7 L) was heated at the reflux temp. with azeotropic removal of water until the theoretical amount of water had been collected (41.4 mL). The reaction mixture was concentrated to 700 mL by simple distillation, then cooled to room temp. and concentrated to constant weight under reduced pressure to give 6-aza-12-oxadispiro[4.1.4.2]tridecane (414 g, 100%) as a pale yellow oil: 1H NMR (CDCl3) δ1.55-1.89 (m, 17H), 3.60 (s, 2H).

Workup

  1. customwith azeotropic removal of water until the theoretical amount of water
  2. customhad been collected (41.4 mL)
  3. concentrationThe reaction mixture was concentrated to 700 mL by simple distillation
  4. temperaturecooled to room temp.
  5. concentrationconcentrated to constant weight under reduced pressure

Sources & evidence

ORD record
ord-6feaf84fefb24715bfd05c33c80baf6a
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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