Triethylamine → Methyl 4-[(pyridine-3-ylmethyl)-amino]-cyclohexane-carboxylate

HRID 2233150Notes

Reaction equation

HRID 2233150 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.C(N(CC)CC)C.[NH2:16][CH:17]1[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH3:26])=[O:24])[CH2:19][CH2:18]1>[Ni].CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:16][CH:17]2[CH2:18][CH2:19][CH:20]([C:23]([O:25][CH3:26])=[O:24])[CH2:21][CH2:22]2)[CH:2]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 103713-PyridinecarboxaldehydeHCID 422580Methyl 4-aminocyclohexanecarboxylate

Product 1

HCID 68583226Methyl 4-[(pyridine-3-ylmethyl)-amino]-cyclohexane-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

6.13 g of pyridine-3-aldehyde, 5.77 g of triethylamine and 9 g of methyl 4-amino-cyclohexanecarboxylate are mixed into 250 ml of methanol. 3 g of Raney nickel are added thereto un order to hydrogenate the mixture, with stirring, for about 6.5 hours at 50° C. and 3 bar. After the catalyst has been eliminated by suction filtering the filtrate is evaporated down. The crude product is purified through silica gel with methylene chloride/methanol.

Workup

  1. filtrationfiltering the filtrate
  2. customis evaporated down
  3. customThe crude product is purified through silica gel with methylene chloride/methanol

Sources & evidence

ORD record
ord-40a8466350574c78aea53dd866976758
Source dataset
uspto-grants-2010_05
Patent number
US07709480B2

Reaction notes

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