Triethylamine → 1-(5-Bromopyridin-3-yl)-N,N-dimethylmethanamine

HRID 1507094Notes

Reaction equation

HRID 1507094 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=O.Cl.[CH3:11][NH:12][CH3:13].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(=O)(O)[O-].[Na+].C(Cl)Cl>[Br:1][C:2]1[CH:9]=[C:6]([CH2:7][N:12]([CH3:13])[CH3:11])[CH:5]=[N:4][CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 116656711-(5-Bromopyridin-3-yl)-N,N-dimethylmethanamineYield 89%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

5-Bromonicontinaldehyde (XXV) (5.01 g, 26.9 mmol) and dimethylamine hydrochloride (4.39 g, 53.8 mmol) were suspended in 1,2-dichloroethane (108 mL). Triethylamine (7.50 mL, 53.8 mmol) was added, and the reaction was stirred at room temperature for 1 h. Sodium triacetoxyborohydride (8.56 g, 40.4 mmol) was added, and the reaction was further stirred at room temperature overnight. The reaction was diluted with saturated sodium bicarbonate solution and DCM. The organic layer was separated, washed sequentially with water and brine, dried over MgSO4, filtered and concentrated to give 1-(5-bromopyridin-3-yl)-N,N-dimethylmethanamine (LIV) (1.19 g, 23.9 mmol, 89% yield) as a brown oil: 1H NMR (DMSO-d6) δ ppm 8.59 (d, J=3 Hz, 1H), 8.47 (d, J=2 Hz, 1H), 7.94 (s, 1H), 3.43 (s, 2H), 2.15 (s, 6H); ESIMS found for C8H11BrN2 m/z 215 (M+H).

Workup

  1. stirringthe reaction was further stirred at room temperature overnight
  2. customThe organic layer was separated
  3. washwashed sequentially with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e81b86018bc74c90ab49d47996424b4b
Source dataset
uspto-grants-2015_12
Patent number
US09221793B2

Reaction notes

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