2-Aminomethyl-1-ethylpyrrolidine → Benzyl Alcohol

HRID 372205Notes

Reaction equation

HRID 372205 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([O:11]C)=O)=[CH:7][N:6]=[CH:5][CH:4]=1.[CH2:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][NH2:21])[CH3:14]>C1(C)C(C)=CC=CC=1>[CH2:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[CH2:20][NH:21][C:9](=[O:11])[C:8]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[N:6][CH:7]=1)[CH3:14].[C:8]1([CH2:9][OH:11])[CH:3]=[CH:4][CH:5]=[CH:13][CH:7]=1

Participants

5

Reactant 2

HCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 10678657Methyl 4-Methoxynicotinate

Product 2

HCID 244Benzyl AlcoholHCID 305004565515-22-2

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

6.7 g (0.04 mole) of methyl 4-methoxynicotinate (m.p. 82°-83° C, W. C. J. Ross, J. Chem. Soc. 1966, 1816) and 7.18 g (0.06 mole) of 1-ethyl-2-(aminomethyl)-pyrrolidine are dissolved in 50 ml of xylene and the solution is heated for 6 hours so that a slow distillation takes place. Approx. 15 ml of distillate with a boiling point of 60°-80° C are collected. The mixture is then completely concentrated in a high vacuum at 50°-60° C and the oily residue obtained is chromatographed through a column of 200 g of basic silica gel. Pure N-[(1-ethyl-2-pyrrolidinyl)-methyl]-4-methoxynicotinamide is obtained as an oil with benzene-methanol (99:1) as eluant.

Workup

  1. temperaturethe solution is heated for 6 hours so that a slow distillation
  2. distillationApprox. 15 ml of distillate with a boiling point of 60°-80° C are collected
  3. concentrationThe mixture is then completely concentrated in a high vacuum at 50°-60° C
  4. customthe oily residue obtained
  5. customis chromatographed through a column of 200 g of basic silica gel

Sources & evidence

ORD record
ord-82b6de0456704672967452ff79dfbed7
Source dataset
uspto-grants-1978_05
Patent number
US04089960

Reaction notes

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