Triethylamine → HCID 58266477, compound

HRID 1505900Notes

Reaction equation

HRID 1505900 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH3:10][N:11]([CH3:18])[CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C>C1COCC1.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:15]2[CH2:16][CH2:17][CH:12]([N:11]([CH3:18])[CH3:10])[CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 685274-Bromobenzyl bromideHCID 417391N,N-Dimethylpiperidin-4-amine

Product 1

HCID 58266477HCID 58266477, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Bromobenzyl bromide (0.5 g, 2.0 mmol) was stirred with 4-dimethylaminopiperidine (0.51 g, 4.0 mmol) and triethylamine (0.42 mL, 3.0 mmol) in THF (20 mL) at ambient temperature for 96 h. The mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound (0.51 g, 86%). 1H NMR (CDCl3, 400 MHz): 7.44-7.40 (m, 2H), 7.21-7.16 (m, 2H), 3.43 (s, 2H), 2.91-2.85 (m, 2H), 2.27 (s, 6H), 2.17-2.07 (m, 1H), 2.00-1.91 (m, 2H), 1.80-1.72 (m, 2H), 1.58-1.45 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-0a587b1bea3441abad819dba3424e242
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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