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

HRID 1505909Notes

Reaction equation

HRID 1505909 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-941032d0f47b42a091c6eaacfe1f3e2c
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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