Ethylamine hydrochloride → 1-benzyl-N-ethylpiperidine-4-carboxamide

HRID 361839Notes

Reaction equation

HRID 361839 reaction equation
Cl.[CH2:2]([NH2:4])[CH3:3].C[Al](C)C.[CH2:9]([N:16]1[CH2:21][CH2:20][CH:19]([C:22](OCC)=[O:23])[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1>[CH2:2]([NH:4][C:22]([CH:19]1[CH2:18][CH2:17][N:16]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:21][CH2:20]1)=[O:23])[CH3:3]

Participants

5

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 90423Ethyl 1-benzylpiperidine-4-carboxylateHCID 16682925Trimethylaluminum

Product 1

HCID 272346131-benzyl-N-ethylpiperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Ethylamine hydrochloride (6.59 g, 80.8 mmol) is dissolved in 40 ml dry toluene and cooled to 0°. Trimethylaluminum (2M in toluene, 40.4 ml, 80.8 mmol) is slowly added and after 30 min at 0° the mixture is warmed to 20°-25°. After one hr gas evolution has ceased. Then ethyl 1-benzylpiperidine-4-carboxylate (10.0 g, 40.4 mmol) is added in 20 ml of toluene and the mixture is heated to 85° for 2 hr. The reaction is quenched cautiously with 5% hydrochloric acid, then adjusted to pH 8 with sodium hydroxide and extracted with chloroform. The extract is dried over sodium sulfate, filtered and evaporated to give the title compound; NMR (300 MHz, CDCl3) 7.32, 3.58, 3.27, 3.00, 2.0-2.2, 1.7-2.0 and 1.11δ.

Workup

  1. temperaturecooled to 0°
  2. temperatureis warmed to 20°-25°
  3. temperaturethe mixture is heated to 85° for 2 hr
  4. customThe reaction is quenched cautiously with 5% hydrochloric acid
  5. extractionextracted with chloroform
  6. dry with materialThe extract is dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ad78daf218ec4ea28fa7205cf036efb6
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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