Triethylamine → N-(2-Pyrimidinyl)-4-phenyl-4-carboethoxy piperidine

HRID 1065216Notes

Reaction equation

HRID 1065216 reaction equation
[C:1]1([C:7]2([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1.Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[N:27]1[CH:28]=[CH:29][CH:30]=[N:31][C:26]=1[N:10]1[CH2:9][CH2:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 32414NormeperidineHCID 744042-Chloropyrimidine

Product 1

HCID 12850326N-(2-Pyrimidinyl)-4-phenyl-4-carboethoxy piperidineYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 4.0 gms (0.017 mole) 4-phenyl-4-carboethoxy-piperidine and 1.72 gms (0.017 mole) of triethylamine in 50 ml. toluene was added dropwise 2.0 gms (0.017 mole) 2-chloropyrimidine. Triethylamine hydrochloride started to precipitate out almost immediately. The reaction mixture was warmed to 70°-80° for a period of two hours, and then allowed to cool. The triethylamine hydrochloride was filtered off and the filtrate washed with water (to remove the last traces of triethylamine hydrochloride). The residue was recrystallized from acetone to yield 2.5 gms (47% yield), m.p. 119°-120°.

Workup

  1. customto precipitate out almost immediately
  2. temperatureThe reaction mixture was warmed to 70°-80° for a period of two hours
  3. temperatureto cool
  4. filtrationThe triethylamine hydrochloride was filtered off
  5. washthe filtrate washed with water (
  6. customto remove the last traces of triethylamine hydrochloride)
  7. customThe residue was recrystallized from acetone
  8. customto yield 2.5 gms (47% yield), m.p. 119°-120°

Sources & evidence

ORD record
ord-4e00a0d417b749e489d8d02994935bfc
Source dataset
uspto-grants-1982_05
Patent number
US04329345

Reaction notes

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