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

HRID 444836Notes

Reaction equation

HRID 444836 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 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-53e048b270bd4d2e8cadf9673a414674
Source dataset
uspto-grants-2013_07
Patent number
US08476267B2

Reaction notes

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