Diisopropylethylamine → Tert-butyl 3-[(5-cyanopyridin-2-yl)amino]piperidine-1-carboxylate

HRID 2171511Notes

Reaction equation

HRID 2171511 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.Cl[C:16]1[N:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C>CS(C)=O>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([NH:1][CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)=[N:21][CH:20]=1)#[N:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5458091-BOC-3-AminopiperidineHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 57911756Tert-butyl 3-[(5-cyanopyridin-2-yl)amino]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

1.0 g (4.99 mmol) of tert-butyl 3-aminopiperidine-1-carboxylate and 1.383 g (9.99 mmol) of 6-chloropyridine-3-carbonitrile and 1.29 g (9.99 mmol) of diisopropylethylamine are suspended in 40 ml of DMSO and heated in a microwave at 140° C. for 45 min. The mixture is substantially freed of DMSO by kugelrohr distillation, water is added, and the precipitate which separates out is filtered off. Drying under high vacuum results in 2.24 g (46% of theory) of the product.

Workup

  1. distillationThe mixture is substantially freed of DMSO by kugelrohr distillation, water
  2. additionis added
  3. filtrationthe precipitate which separates out is filtered off
  4. customDrying under high vacuum
  5. customresults in 2.24 g (46% of theory) of the product

Sources & evidence

ORD record
ord-c86405c236144cdb855ed578264aa1c1
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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