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

HRID 1183052Notes

Reaction equation

HRID 1183052 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].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C(Cl)Cl.C([O-])(O)=O.[Na+]>[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

7

Reactant 3

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

Product 1

HCID 116656711-(5-Bromopyridin-3-yl)-N,N-dimethylmethanamineYield 92.6%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-bromonicotinaldehyde (XLV) (5.0 g, 26.9 mmol) in DCE (108 mL) was added dimethylamine-HCl (4.39 g, 53.8 mmol) and TEA (7.5 g, 53.8 mmol). The reaction was stirred at room temperature for 1 h. NaBH(OAc)3 was added and the reaction was stirred overnight at room temperature. The reaction was diluted with DCM and sat. aq. NaHCO3. The organic layer was separated, washed with water, brine, dried and concentrated under vacuum to produce 1-(5-bromopyridin-3-yl)-N,N-dimethylmethanamine (XLVI) as a brown liquid (5.36 g, 24.9 mmol, 92.6% yield). 1H NMR (CDCl3) δ ppm 2.15 (s, 6H), 3.43 (s, 2H), 7.94 (s, 1H), 8.47 (d, J=1.1 Hz, 1H), 8.59 (d, J=2.2 Hz, 1H); ESIMS found C8H11BrN2 m/z 215 (MBr79+H) and 217 (MBr81+H).

Workup

  1. stirringthe reaction was stirred overnight at room temperature
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. customdried
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-08c715d2eb4e4f919856a9bb8d2911f1
Source dataset
uspto-grants-2014_03
Patent number
US08664241B2

Reaction notes

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