Thionyl Chloride → N,N-dimethylpyridin-4-amine Hydrochloride

HRID 975269Notes

Reaction equation

HRID 975269 reaction equation
S(Cl)([Cl:3])=O.CC1C[CH2:10][N:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH2:8]C1.Cl.CC1CCN(C2C=CN=CC=2)CC1>CN(C)C1C=CN=CC=1>[ClH:3].[CH3:8][N:9]([CH3:10])[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 157352Pyridine, 4-(4-methyl-1-piperidinyl)-HCID 13163133HCID 13163133, compound

Product 1

HCID 11789490N,N-dimethylpyridin-4-amine Hydrochloride

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A process for the preparation of the compound of Formula I ##STR10## which comprises Step (a) treating the compound of Formula Va ##STR11## with thionyl chloride in the presence of a 4-N,N'-disubstituted aminopyridine selected from the group consisting of 4-(4-methyl-1-piperidinyl)pyridine; 4-(4-methyl-1-piperidinyl)pyridine hydrochloride; 4-dimethylaminopyridine; and 4-dimethylaminopyridine hydrochloride and a solvent to afford the compound of Formula IVa; ##STR12## Step (b) treating the compound of Formula IVa with sodium isopropoxide in a solvent followed by saponification with a base to afford the compound of Formula III; ##STR13## Step (c) treating the compound of Formula III in a solvent with thionyl chloride and pyridine in a solvent and subsequently adding 5-aminotetrazole and triethylamine in a solvent to afford the compound of Formula II; ##STR14## Step (d) treating the compound of Formula II with sodium hydroxide solution in a solvent to afford the compound of Formula I.

Workup

  1. customA process for the preparation of the compound of Formula I ##STR10## which
  2. additiontreating the compound of Formula Va

Sources & evidence

ORD record
ord-466374729c8247a19e95b74e63d15599
Source dataset
uspto-grants-1997_03
Patent number
US05608074

Reaction notes

Loading…