3-Pyridinemethanamine → (-)-Anatabine

HRID 884326Notes

Reaction equation

HRID 884326 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[C:9](=N)([C:16]1C=CC=CC=1)[C:10]1C=CC=C[CH:11]=1>>[CH2:16]1[C@@H:2]([C:3]2[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=2)[NH:1][CH2:11][CH:10]=[CH:9]1

Participants

3

Reactant 2

HCID 310183-PyridinemethanamineHCID 136809Benzophenone imine

Product 1

HCID 11388(-)-Anatabine

Procedure

3-aminomethylpyridine was added to neat benzophenoneimine (1 eq). The reaction was allowed to proceed for 6 hours at 50° C. providing Formula I as the product.

Workup

  1. customproviding Formula I as the product

Sources & evidence

ORD record
ord-157b88ca22f049d987ab7c60a1ab276c
Source dataset
uspto-grants-2012_08
Patent number
US08241680B2

Reaction notes

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