Ammonia → HCID 15663632, compound

HRID 1587374Notes

Reaction equation

HRID 1587374 reaction equation
[N+](C1C=C(C=CC=1)C([N:9]1[CH:13]=[C:12]([C:14]23[CH2:20][N:17]([CH2:18][CH2:19]2)[CH2:16][CH2:15]3)[N:11]=[N:10]1)=O)([O-])=O.N>CO>[N:9]1[NH:10][N:11]=[C:12]([C:14]23[CH2:20][N:17]([CH2:18][CH2:19]2)[CH2:16][CH2:15]3)[CH:13]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19757983HCID 19757983, compound

Product 1

HCID 15663632HCID 15663632, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(1-m-nitrobenzoyl-1,2,3-triazol-4-yl)-1-azabicyclo[2.2.1]heptane (D25) (1 g, 0.0032 mole) in methanol (50 ml) was saturated with ammonia gas. The solution allowed to stand at room temperature for 3 days and then concentrated in vacuo to a gum. The gum was chromatographed on alumina in a gradient of 10-20% methanol in chloroform, elution with 15% methanol in chloroform produced a gum which crystallised from ethyl acetate to afford the title compound (D26, 450mg, 0.0027 mole, 85%).

Workup

  1. concentrationconcentrated in vacuo to a gum
  2. customThe gum was chromatographed on alumina in a gradient of 10-20% methanol in chloroform, elution with 15% methanol in chloroform
  3. customproduced a gum which
  4. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-bb4a6fdb6eca46c5b4b42e0b2f4a0ee3
Source dataset
uspto-grants-1993_06
Patent number
US05217975

Reaction notes

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