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

HRID 2088654Notes

Reaction equation

HRID 2088654 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 were suspended in 40 ml of DMSO and heated in a microwave reactor at 140° C. for 45 min. Most of the DMSO was removed from the mixture by kugelrohr distillation, water was added and the resulting precipitate was filtered off. Drying under high vacuum gave 2.24 g (46% of theory) of the product.

Workup

  1. customMost of the DMSO was removed from the mixture by kugelrohr distillation, water
  2. additionwas added
  3. filtrationthe resulting precipitate was filtered off
  4. customDrying under high vacuum
  5. customgave 2.24 g (46% of theory) of the product

Sources & evidence

ORD record
ord-0584f07c6e8e4b1fbfe74113c724b5a3
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

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