Methyl formate → N-benzyl-N-methyl-5-(4-aminomethylpiperidin-1-yl)pentylamine

HRID 344437Notes

Reaction equation

HRID 344437 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH:21]C(OC(C)(C)C)=O)[CH2:16][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:29](OC)=O>>[CH2:1]([N:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([CH2:20][NH2:21])[CH2:18][CH2:19]1)[CH3:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 7865Methyl formateHCID 54349226HCID 54349226, compound

Product 1

HCID 53908674N-benzyl-N-methyl-5-(4-aminomethylpiperidin-1-yl)pentylamine

Procedure

A solution of N-benzyl-5-(4-tert-butoxycarbonylaminomethylpiperidin-1-yl)pentylamine (3.7 g) in methyl formate (30 ml) was refluxed under heating for 12 hr. After cooling, methyl formate was evaporated, and tetrahydrofuran (40 ml) and 2M trifluoroborane-dimethyl sulfide solution (19 ml) were added to the residue, which was followed by refluxing under heating for 6 hr. The solvent was evaporated, and ethanol (40 ml) and hydrochloric acid (3 ml) were added to the reaction mixture, which was followed by refluxing under heating for 3 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure to give 3.60 g of N-benzyl-N-methyl-5-(4-aminomethylpiperidin-1-yl)pentylamine.

Workup

  1. temperatureunder heating for 12 hr
  2. temperatureAfter cooling
  3. custommethyl formate was evaporated
  4. additiontetrahydrofuran (40 ml) and 2M trifluoroborane-dimethyl sulfide solution (19 ml) were added to the residue, which
  5. temperatureby refluxing
  6. temperatureunder heating for 6 hr
  7. customThe solvent was evaporated
  8. additionethanol (40 ml) and hydrochloric acid (3 ml) were added to the reaction mixture, which
  9. temperatureby refluxing
  10. temperatureunder heating for 3 hr
  11. temperatureAfter cooling
  12. additionwater was added to the reaction mixture
  13. extractionthe mixture was extracted with ethyl acetate
  14. washThe organic layer was washed with brine
  15. customdried
  16. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-961b13a2a49b4e9a84ad86d42ce9c2f8
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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