Ammonia → alpha-(Aminomethyl)-2,2-dimethyl-1,3-dioxolane-4-methanol

HRID 464238Notes

Reaction equation

HRID 464238 reaction equation
[CH3:1][C:2]1([CH3:10])[O:6][CH:5]([CH:7]2[O:9][CH2:8]2)[CH2:4][O:3]1.[NH3:11]>>[NH2:11][CH2:8][CH:7]([CH:5]1[CH2:4][O:3][C:2]([CH3:10])([CH3:1])[O:6]1)[OH:9]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 131868272,2-Dimethyl-4-(oxiran-2-YL)-1,3-dioxolane

Product 1

HCID 11971028alpha-(Aminomethyl)-2,2-dimethyl-1,3-dioxolane-4-methanol

Procedure

A solution of 73.4 g of 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethylene oxide in 400 ml of 25% strength ammonia is heated in an autoclave for 4 hours to 130° C. The slightly yellowish solution is concentrated to dryness under vacuum; during this step, the residue crystallizes. 2-Amino-1-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol is re-crystallized from ethanol/ether, mp 94°-96° C.

Workup

  1. concentrationThe slightly yellowish solution is concentrated to dryness under vacuum
  2. customduring this step, the residue crystallizes
  3. custom2-Amino-1-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol is re-crystallized from ethanol/ether, mp 94°-96° C.

Sources & evidence

ORD record
ord-723c62d451c546768f0eec4af71fdfde
Source dataset
uspto-grants-1985_10
Patent number
US04547357

Reaction notes

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