Potassium Carbonate → 1-[2-(2-Methoxyphenoxy)ethyl]-4-benzamidopiperidine

HRID 1730361Notes

Reaction equation

HRID 1730361 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[O:5][CH2:6][CH2:7]Br.[C:13]([NH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[O:5][CH2:6][CH2:7][N:25]1[CH2:26][CH2:27][CH:22]([NH:21][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 118120N-4-PiperidylbenzamideHCID 17990992-(2-Bromoethoxy)anisole

Product 1

HCID 214305691-[2-(2-Methoxyphenoxy)ethyl]-4-benzamidopiperidineYield 83.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(2-Methoxyphenoxy)ethyl bromide (2.31 g.), 4-benzamidopiperidine (2.04 g.) and anhydrous potassium carbonate (1.38 g.) were well mixed and heatedon a steam bath for 4 hr. The resulting mass was crushed and stirred in water (200 ml.) at 60° for 12 hr. Filtration afforded the crude base of the title compound (2.95 g.). Conversion to the hydrochloride by solution in ethanol/HCl and precipitation with ether provided 3.01 g. of the title compound, as the hydrochloride m.p. 193.4°. Analysis : Found C, 64.74; H, 7.08; N, 7.14. C21H26N2O3. HCl requires C, 64.52; H, 6.96; N, 7.17%.

Workup

  1. customThe resulting mass was crushed
  2. filtrationFiltration

Sources & evidence

ORD record
ord-6efa4f0693784474bab4714b5292cf89
Source dataset
uspto-grants-1976_11
Patent number
US03992389

Reaction notes

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