4-Methylpiperidin-4-ol → 3-Pyridinecarbonitrile, 6-amino-4-(4-hydroxy-4-methyl-1-piperidinyl)-

HRID 1777889Notes

Reaction equation

HRID 1777889 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8](Cl)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[OH:11][C:12]1([CH3:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>CC(N(C)C)=O>[NH2:1][C:2]1[CH:9]=[C:8]([N:15]2[CH2:16][CH2:17][C:12]([OH:11])([CH3:18])[CH2:13][CH2:14]2)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 156491744-Methylpiperidin-4-olHCID 219492196-Amino-4-chloro-3-pyridinecarbonitrile2×

Product 1

HCID 1180369033-Pyridinecarbonitrile, 6-amino-4-(4-hydroxy-4-methyl-1-piperidinyl)-

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 6-amino-4-chloronicotinonitrile (intermediate 16, 31.6 mg, 0.206 mmol) and 4-hydroxy-4-methylpiperidine (47.4 mg, 0.412 mmol) in DMA (0.75 ml) was heated to 100° C. and stirred for 1 h. The resulting brown solution was heated to 120° C. and stirred for 18 h.

Workup

  1. temperatureThe resulting brown solution was heated to 120° C.
  2. stirringstirred for 18 h.

Sources & evidence

ORD record
ord-b1a95c67082545368851d8f70bbc6743
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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