HCID 178501222, compound → HCID 178501207, compound

HRID 1490119Notes

Reaction equation

HRID 1490119 reaction equation
C([N:8]([C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH2:13]1)CCO)C1C=CC=CC=1>CO.[Pd]>[NH2:8][C@H:12]1[CH2:13][CH2:14][C@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][CH2:17]1

Participants

4

Reactant 1

HCID 178501222HCID 178501222, compound

Product 1

HCID 178501207HCID 178501207, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

13 g of methyl trans-4-[N-benzyl-N-(2-hydroxyethyl)amino]-cyclohexanecarboxylate are hydrogenated in 150 ml of methanol with 3.5 g of palladium on activated charcoal (10% palladium) under a hydrogen pressure of 50 psi for 20 minutes at 50° C. The catalyst is suction filtered and the filtrate is evaporated to dryness. (The starting material is obtained from methyl trans-4-amino-cyclohexanecarboxylate by reacting with benzaldehyde and hydrogen in the presence of Raney-nickel and subsequently reacting with 2-bromoethanol in the presence of N-ethyl-diisopropylamine).

Workup

  1. customfor 20 minutes
  2. customat 50° C
  3. filtrationfiltered
  4. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-5ec08fae12ba481dab6f4f32c2cc1e03
Source dataset
uspto-grants-1997_10
Patent number
US05681841

Reaction notes

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