Triethylamine → 1-(4-Bromobenzyl)-4-methoxy-4-methylpiperidine

HRID 1888446Notes

Reaction equation

HRID 1888446 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][O:18][C:19]1([CH3:25])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:22]2[CH2:23][CH2:24][C:19]([O:18][CH3:17])([CH3:25])[CH2:20][CH2:21]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685274-Bromobenzyl bromideHCID 203737104-Methoxy-4-methylpiperidine

Product 1

HCID 582666131-(4-Bromobenzyl)-4-methoxy-4-methylpiperidineYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-bromobenzyl bromide (0.44 g, 1.74 mmol), triethylamine (0.37 mL, 2.61 mmol) and 4-methoxy-4-methylpiperidine (0.45 g, 3.49 mmol)in THF (10 mL) was stirred at ambient temperature for 16 h. The solvent was evaporated and the resultant residue was diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over sodium sulfate, filtered and evaporated to afford the title compound as a yellow oil (0.50 g, 96%). 1H NMR (CDCl3, 300 MHz): 7.45-7.39 (m, 2H), 7.22-7.17 (m, 2H), 3.44 (s, 2H), 3.17 (s, 3H), 2.52-2.42 (m, 2H), 2.36-2.25 (m, 2H), 1.79-1.70 (m, 2H), 1.59-1.47 (m, 2H), 1.13 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. additionthe resultant residue was diluted with saturated aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-003ab9f4047746d79aa35d2d0236f0f7
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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