Benzylamine → HCID 21241591, compound

HRID 579800Notes

Reaction equation

HRID 579800 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18](=O)[CH3:19])[CH2:14][CH2:13]1.[C:21]1([CH2:27][NH2:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.S1C=CC=C1.[H][H]>CO.[Pd]>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([CH:18]([CH3:19])[NH:28][CH2:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8030ThiopheneHCID 21241598HCID 21241598, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21241591HCID 21241591, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 10 parts of 1-[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]ethanone, 3.8 parts of benzenemethanamine, 1 part of a solution of thiophene in methanol 4% and 160 parts of methanol was hydrogenated at normal pressure and at 50° C. with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 13.2 parts (100%) of 1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-α-methyl-N-(phenylmethyl)-4-piperidinemethanamine as an oily residue (intermediate 88).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a4003ed443e64dedaab980ec4b337740
Source dataset
uspto-grants-1988_06
Patent number
US04749702

Reaction notes

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