2-Phenylnicotinic acid → 2-Phenylpiperidin-3-amine

HRID 1830833Notes

Reaction equation

HRID 1830833 reaction equation
C1(C2N=CC=CC=2C(O)=O)C=CC=CC=1.[C:16]1([C:22]2[C:27]([NH2:28])=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:16]1([CH:22]2[CH:27]([NH2:28])[CH2:26][CH2:25][CH2:24][NH:23]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 974892-Phenylnicotinic acidHCID 27627843-Amino-2-phenylpyridine

Product 1

HCID 97940082-Phenylpiperidin-3-amine

Procedure

First, a carboxyl group of a 2-phenylnicotinic acid derivative is amidated and applied to Hofmann's reaction. Then, the resulting 2-phenyl-3-aminopyridine derivative is reduced to produce a 2-phenyl-3-aminopiperidine derivative, and further subjecting the resulting compound to acylation or alkylation, if desired.

Workup

  1. customapplied to Hofmann's reaction

Sources & evidence

ORD record
ord-d470a022d26b4b1aba454715856cc860
Source dataset
uspto-grants-2006_06
Patent number
US07067535B2

Reaction notes

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