Ammonium Chloride → 1-Azabicyclo[2.2.1]heptan-4-ylmethanamine

HRID 1641004Notes

Reaction equation

[N:1]12[CH2:7][C:4]([C:8](OCC)=O)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Cl-].[NH4+:14].C[Al](C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[N:1]12[CH2:7][C:4]([CH2:8][NH2:14])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2

Participants

Reactant 4

HCID 25517Ammonium Chloride

HCID 15663604Ethyl 1-azabicyclo[2.2.1]heptane-4-carboxylate

HCID 16682925Trimethylaluminum

HCID 21226445Aluminium lithium hydride

Product 1

HCID 552901901-Azabicyclo[2.2.1]heptan-4-ylmethanamine

Procedure

1-Azabicyclo[2.2.1]heptan-4-ylmethanamine was prepared by treatment of ethyl 1-azabicyclo[2.2.1]heptane-4-carboxylate with ammonium chloride and trimethylaluminum and reducing the resulting amide with lithium aluminum hydride.

Sources & evidence

ORD record: ord-a86dc073bb784a24b75d70f6d896622e
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114891B2

Reaction notes

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