2-Benzyl-1-(1-pyrrolidinylmethyl)-1,2,3,4-tetrahydroisoquinoline → 1-(Pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1382233Notes

Reaction equation

HRID 1382233 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[CH2:18][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)C1C=CC=CC=1>C(O)C.[Pd]>[N:19]1([CH2:18][CH:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:16][CH2:17][NH:8]2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 1

HCID 212745372-Benzyl-1-(1-pyrrolidinylmethyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 147260101-(Pyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydroisoquinolineYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

8 g of 2-benzyl-1-(1-pyrrolidinylmethyl)-1,2,3,4-tetrahydroisoquinoline were dissolved in 200 ml of 95% ethanol and hydrogenated on 1.5 g of 5% Pd on charcoal at 40° C. and room temperature. After 7 hr the catalyst was filtered off, and the solvent evaporated i.v. 5.5 g of crude product were obtained, sufficiently pure for the subsequent step.

Workup

  1. filtrationAfter 7 hr the catalyst was filtered off
  2. customthe solvent evaporated i.v

Sources & evidence

ORD record
ord-3f80a31861a04eb2a0894854f512516f
Source dataset
uspto-grants-1989_02
Patent number
US04806547

Reaction notes

Loading…