3-Pyridinecarboxaldehyde → HCID 43182253, compound

HRID 392448Notes

Reaction equation

HRID 392448 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([NH2:8])[CH3:7])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=O)[CH:12]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([NH:8][CH2:17][C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[CH3:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 911751-(4-Bromophenyl)ethylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43182253HCID 43182253, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-α-methylbenzylamine (1.5 g, 7.7 mmol), 3-pyridinecarboxaldehyde (0.8 g, 7.5 mmol), and sodium triacetoxyborohydride (2.25 g, 10.5 mmol) in 60 ml of 1,2-dichloroethane was stirred at room temperature for 18 h. The solution was diluted with dichloromethane and washed twice with a saturated sodium bicarbonate solution, once with water, and once with brine. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound. 1H NMR: 8.70 (m,2H), 7.85 (m,1H), 7.67 (d,2H,J=8 Hz), 7.45 (d,2H,J=8 Hz), 7.43 (m,1H), 3.95 (q,1H,J=8 Hz), 3.83 (q,ABX,2H), 1.57 (d,3H,J=8 Hz). MS calcd. 291.2; MS (M+1) 292.1.

Workup

  1. washwashed twice with a saturated sodium bicarbonate solution, once with water
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b79e6569323d44a28508556b25de030c
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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