Piperidine → 5-Bromo-3-piperidin-1-ylmethyl-pyridin-2-ylamine

HRID 1362097

Reaction equation

HRID 1362097 reaction equation
Br.[Br:2][C:3]1[CH:4]=[C:5]([CH2:10]Br)[C:6]([NH2:9])=[N:7][CH:8]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CC#N.CCOCC>[Br:2][C:3]1[CH:4]=[C:5]([CH2:10][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:6]([NH2:9])=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

Product 1

HCID 594569835-Bromo-3-piperidin-1-ylmethyl-pyridin-2-ylamineYield 53.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

An ice-cold suspension of 5-bromo-3-bromomethyl-pyridin-2-ylamine hydrobromide (10.0 g, 28.8 mmol) in MeCN (100 mL) was treated with piperidine (6.4 mL, 64.8 mmol). After stirring at room temperature for 3.5 h, the mixture was diluted with Et2O (500 mL). The solution was filtered and then concentrated to give the title compound (4.16 g, 53%) as a pale, yellow solid: MS (ESI) m/e 270 (M+H)+.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7b1adbb30ca24a069da8dc51c1197c74
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Linked notes

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