Ethanol → HCID 13046887, compound

HRID 647824Notes

Reaction equation

HRID 647824 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)C.[H][H]>[C].[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 702EthanolHCID 13046886tert-Butyl 4-{[(2-nitrophenyl)methyl]amino}piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 13046887HCID 13046887, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In this reference example, 40 g of 1-tert.-butoxycarbonyl-4-(2-nitrophenylmethylamino)-piperidine obtained in the same manner as that of Reference Example 6, 100 ml of ethanol, 60 ml of methanol and 4 g of palladium carbon are mixed. The mixture is shaken in an atmosphere of hydrogen at room temperature under 40-45 psi. The catalyst is filtered off and the filtrate is concentrated to obtain 35.1 g of oily material as the residue. The residue is crystallized with the addition of n-hexane to obtain 28.3 g of the crude crystals. Though the crude crystals are usable to the following reaction, a part of the crystals is recrystallized from n-hexane to obtain the desired compound.

Workup

  1. additionare mixed
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-b666179986ed4473bb9978e96872b3e3
Source dataset
uspto-grants-1983_10
Patent number
US04410528

Reaction notes

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