Hydrochloric Acid → 5-(4-Amino-1-piperidinyl)-3-pyridinecarbonitrile

HRID 475358Notes

Reaction equation

HRID 475358 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:20]#[N:21])[CH:19]=2)[CH2:10][CH2:9]1)(C)(C)C.Cl>O1CCOCC1>[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:20]#[N:21])[CH:19]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66756810HCID 66756810, compound

Product 1

HCID 667564155-(4-Amino-1-piperidinyl)-3-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of (5′-cyano-3,4,5,6-tetrahydro-2H-(1,3′)bipyridinyl-4-yl)-carbamic acid tert-butyl ester (0.45 g, 1.49 mmol) in dioxane (3.0 mL) at room temperature was added 4M HCl in dioxane (8 mL). The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was treated with ether. The solid obtained by filtration provided the titled compound. MS (CI) m/z 203 (M+1)+; 1H NMR (300 MHz, methanol-d4) δ ppm 8.68 (d, 1H), 8.52 (s, 1H), 8.35 (m, 1H), 4.15-4.10 (m, 2H), 3.51-3.40 (m, 1H), 3.12 (t, 2H), 2.20-2.15 (m, 2H), 1.82-1.69 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was treated with ether
  3. customThe solid obtained by filtration

Sources & evidence

ORD record
ord-560b676b4a424a2c911ac87b8fe2ca36
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

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