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

HRID 1182993Notes

Reaction equation

HRID 1182993 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 to 140° C. in a microwave reactor for 45 min. The mixture was substantially freed of the DMSO by Kugelrohr distillation and admixed with water, and the precipitating solid was filtered off. After drying under high vacuum, 2.24 g (46% of theory) of the product were obtained.

Workup

  1. distillationThe mixture was substantially freed of the DMSO by Kugelrohr distillation
  2. filtrationthe precipitating solid was filtered off
  3. customAfter drying under high vacuum, 2.24 g (46% of theory) of the product
  4. customwere obtained

Sources & evidence

ORD record
ord-92151802975547a6bc1c359f2c6e7e1b
Source dataset
uspto-grants-2014_03
Patent number
US08664246B2

Reaction notes

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