1-Methylpyrrole → 1-Methyl-4-(1-methylpyrrol-2-yl)-4-piperidinol

HRID 2286515Notes

Reaction equation

HRID 2286515 reaction equation
C([Li])CCC.[CH3:6][N:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1.[CH3:12][N:13]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]1>CCCCCC.C(OCC)C>[CH3:12][N:13]1[CH2:18][CH2:17][C:16]([C:8]2[N:7]([CH3:6])[CH:11]=[CH:10][CH:9]=2)([OH:19])[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 73041-MethylpyrroleHCID 740491-Methyl-4-piperidoneHCID 178418339Butyllithium

Product 1

HCID 1328661-Methyl-4-(1-methylpyrrol-2-yl)-4-piperidinol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A 1.6 M solution of n-butyllithium in hexane (175 ml) was added dropwise at room temperature to a solution of 24.2 g of N-methylpyrrole in 250 ml of diethyl ether contained in a reaction flask (under a nitrogen blanket). After addition was completed, the resulting mixture was heated at reflux with stirring for 16 hours, then cooled to 0° C. 34 Grams of 1-methyl-4-piperidone was added dropwise from a dropping funnel with the temperature maintained at 0° C. during the addition by cooling the reaction flask with dry ice-acetone bath. The reaction mixture was stirred at room temperature for 3 hours, and then quenched in ice water to yield 26 g of the title compound in a crystalline form; recrystallization from heptane gave white prisms, m.p. 123°-123.5°.

Workup

  1. customcontained in a reaction flask
  2. additionAfter addition
  3. temperaturethe resulting mixture was heated
  4. temperatureat reflux
  5. temperaturemaintained at 0° C. during the addition
  6. temperatureby cooling the reaction flask with dry ice-acetone bath
  7. stirringThe reaction mixture was stirred at room temperature for 3 hours
  8. customquenched in ice water

Sources & evidence

ORD record
ord-eb794ca9ba1a48a196889c070acfda3a
Source dataset
uspto-grants-1981_05
Patent number
US04267185

Reaction notes

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