Toluene → N-(2-methoxyethyl)piperidine-4-carboxamide

HRID 1389156Notes

Reaction equation

HRID 1389156 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:23])[NH:18][CH2:19][CH2:20][O:21][CH3:22])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C1(C)C=CC=CC=1.C(OC(N1CCC(C(Cl)=O)CC1)=O)C1C=CC=CC=1.COCCN>C(O)C.[Pd]>[CH3:22][O:21][CH2:20][CH2:19][NH:18][C:17]([CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)=[O:23]

Participants

7

Reactant 4

HCID 1140TolueneHCID 80182-MethoxyethylamineHCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylateHCID 202981261-Benzyloxycarbonyl-4-[N-(2-methoxyethyl)carbamoyl]piperidine

Product 1

HCID 7175816N-(2-methoxyethyl)piperidine-4-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-Benzyloxycarbonyl-4-[N-(2-methoxyethyl)carbamoyl]piperidine [5.76 g, m.p. 85°-86°, Analysis %: C, 63.9; H, 7.5; N, 8.4; Calculated: C, 63.7; H, 7.6; N, 8.8; prepared similarly to Preparation C but using toluene in place of chloroform and starting from 1-benzyloxycarbonylpiperidine-4-carboxylic acid chloride and 2-methoxyethylamine] in ethanol (75 ml) was hydrogenated over 5% palladium on charcoal at 50 p.s.i./50°. The catalyst was removed by filtration, and the filtrate evaporated to give 4-[N-(2-methoxyethyl)carbamoyl]piperidine as an oil which solidified on standing. I.r. and n.m.r. spectra were consistent with this structure and the product was used in Example 7 without further purification.

Workup

  1. customprepared similarly to Preparation C
  2. custom50°
  3. customThe catalyst was removed by filtration
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-ef4a375bc2c94ad8abd5379293b58e1c
Source dataset
uspto-grants-1981_01
Patent number
US04243666

Reaction notes

Loading…