Triethylamine → tert-Butyl4-(3-cyano-2-pyridinyl)-1-piperazinecarboxylate

HRID 1829190Notes

Reaction equation

HRID 1829190 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:8]([C:7]1[C:2]([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)=[N:3][CH:4]=[CH:5][CH:6]=1)#[N:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 810792-ChloronicotinonitrileHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 22061422tert-Butyl4-(3-cyano-2-pyridinyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-chloro-3-cyanopyridine (15.2 g, 0.11 mol), tert-butyl 1-piperazinecarboxylate (25 g, 0.13 mol) and triethylamine (18 ml, 0.13 mol) in toluene (200 ml), was heated under reflux for 24 hours. The cooled mixture was concentrated under reduced pressure and the residue suspended in ethyl acetate (250 ml), and washed with water (3×). The organic solution was dried (MgSO4), and concentrated under reduced pressure. The residue was triturated with pentane, filtered and dried in vacuo, at 60° C., to afford the title compound as a cream coloured solid, 24.2 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. concentrationThe cooled mixture was concentrated under reduced pressure
  4. washwashed with water (3×)
  5. dry with materialThe organic solution was dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with pentane
  8. filtrationfiltered
  9. customdried in vacuo, at 60° C.

Sources & evidence

ORD record
ord-4170c0f4d1d74f3ab1306d06b36dbb36
Source dataset
uspto-grants-2006_06
Patent number
US07060836B2

Reaction notes

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