2,4-Dimethoxybenzylamine → HCID 20298130, compound

HRID 1389163Notes

Reaction equation

HRID 1389163 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17](Cl)=[O:18])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[CH3:20][O:21][C:22]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:23]=1[CH2:24][NH2:25]>C(O)C.[Pd]>[CH3:20][O:21][C:22]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:23]=1[CH2:24][NH:25][C:17]([CH:14]1[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1)=[O:18]

Participants

5

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate

Product 1

HCID 20298130HCID 20298130, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Benzyloxycarbonyl-4-[N-2,4-dimethoxybenzylcarbamoyl]piperidine was prepared similarly to Preparation C starting from 1-benzyloxycarbonylpiperidine-4-carboxylic acid chloride and 2,4-dimethoxybenzylamine. The product was identified by n.m.r. spectroscopy. This product (7.6 g) in ethanol (150 ml) was hydrogenated over 5% palladium on charcoal at 50°/50 p.s.i. The catalyst was removed by filtration and the filtrate evaporated in vacuo to give 4-[N-(2,4-dimethoxybenzyl)carbamoyl]piperidine (5.0 g) as a solid. A sample in chloroform was converted to the hydrochloride salt by treatment with ethereal hydrogen chloride and recrystallised from isopropanol, m.p. 222°-224°.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-6c6801cdce084d99805b31017e7fd459
Source dataset
uspto-grants-1981_01
Patent number
US04243666

Reaction notes

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