Ammonia → 1-Azabicyclo[3.1.1]heptane-5-carboxamide

HRID 466812

Reaction equation

HRID 466812 reaction equation
[N:1]12[CH2:7][C:5]([C:8]([O:10]C)=O)([CH2:6]1)[CH2:4][CH2:3][CH2:2]2.[NH3:12].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[N:1]12[CH2:7][C:5]([C:8]([NH2:12])=[O:10])([CH2:6]1)[CH2:4][CH2:3][CH2:2]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 19814748Methyl 1-azabicyclo[3.1.1]hept-5-ylcarboxylate

Product 1

HCID 198147681-Azabicyclo[3.1.1]heptane-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methyl 1-azabicyclo[3.1.1]hept-5-ylcarboxylate (D4, 1.35 g, 0.0087 mole) was treated with 20M aqueous ammonia solution (25 ml) and the mixture stirred at room temperature for 2 days. The solution was saturated with potassium carbonate and shaken with chloroform (40 ml) The mixture separated into three layers. The chloroform solution contained some product, however the majority was in the middle layer. These two were combined and concentrated in vacuo and the residue then treated with toluene (60 ml) and again concentrated in vacuo to azeotrope out the water. The title compound (D12) remained as a white solid (1.07 g, 88%) m.p. 188°-1920° C.

Workup

  1. customseparated into three layers
  2. concentrationconcentrated in vacuo
  3. additionthe residue then treated with toluene (60 ml)
  4. concentrationagain concentrated in vacuo

Sources & evidence

ORD record
ord-c2d116e29ed4478dadb10cba8e5b15ae
Source dataset
uspto-grants-1992_10
Patent number
US05157160

Linked notes

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