Cyclopentylamine → N-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]cyclopentanamine

HRID 45261Notes

Reaction equation

HRID 45261 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15][CH2:14]2)(=O)=O)=CC=1.[CH:21]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22]1>>[CH3:20][C:16]1([CH3:19])[O:15][CH2:14][CH:13]([CH2:12][NH:26][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:18][O:17]1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 14893699(2,2-Dimethyl-1,3-dioxan-5-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 67455188N-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]cyclopentanamineYield 100%

Conditions

Temperature
80 °C

Procedure

A mixture of 1.5 g (5 mmol) of (2,2-dimethyl-1,3-dioxan-5-yl)methyl 4-methylbenzenesulfonate and 10 mL (101 mmol) of cyclopentylamine is heated for 12 hours at 80° C. The medium is concentrated under reduced pressure and then taken up in 200 mL of Et2O, washed with water (2×50 mL) and then dried over Na2SO4 and concentrated under reduced pressure. 1 g of N-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]cyclopentanamine is obtained in the form of an oil, which is used without further purification in the following step.

Workup

  1. concentrationThe medium is concentrated under reduced pressure
  2. washwashed with water (2×50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-13d651aaf64f4ed5a9f1d4fe8b8f4b27
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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