Triethylamine → HCID 10902638, compound

HRID 1769271Notes

Reaction equation

HRID 1769271 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.NCC[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].ClC1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][N:21]=1.[C]=[O:28]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:26][C:23]1[CH:24]=[CH:25][C:7]([C:6]([NH:3][CH2:4][CH2:5][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:28])=[N:21][CH:22]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 276852,5-DichloropyridineHCID 187201N-BOC-ethylenediamineHCID 178418416HCID 178418416, compound

Product 1

HCID 10902638HCID 10902638, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 1140TolueneSolvent

Procedure

A 250 ml autoclave is charged under an argon atmosphere with 50 ml of toluene, 5.2 ml (37.2 mmol) of triethylamine, 1.2 mg (0.0067 mmol) of palladium chloride, 5.6 mg (0.0135 mmol) of 1,3-bis(diphenylphosphino)propane, 6.5 g (40.56 mmol) of t-butyl (2-aminoethyl)carbamate and 5.0 g (33.8 mmol) of 2,5-dichloropyridine. After repeated evacuation and pressurization with 106Pa of nitrogen the autoclave is gassed with 106Pa of carbon monoxide and heated to 130° while stirring. After heating to 130° for 24 hours the autoclave is cooled, opened and discharged and the orange-brown suspension is filtered through 50 g of silica gel with a 1:1 mixture of toluene and ether as the eluting agent. The fractions containing the desired product (determined by thin-layer chromatography) are combined, evaporated to about 150 ml and stirred vigorously at 70° overnight with a solution of 2 mg of sodium cyanide in 25 ml of water in order to separate the palladium. Thereafter, the organic phase is separated, washed with water and evaporated. Crystallization of the solid residue from toluene/hexane yields 8.51 g (84%) of t-butyl [2-(5-chloropyridine-2-carboxamido)ethyl]carbamate as white crystals, m.p. 106°-108°.

Workup

  1. temperatureheated to 130°
  2. temperatureAfter heating to 130° for 24 hours the autoclave
  3. temperatureis cooled
  4. filtrationthe orange-brown suspension is filtered through 50 g of silica gel with a 1:1 mixture of toluene and ether as the eluting agent
  5. additionThe fractions containing the desired product (determined by thin-layer chromatography)
  6. customevaporated to about 150 ml
  7. stirringstirred vigorously at 70° overnight with a solution of 2 mg of sodium cyanide in 25 ml of water in order
  8. customto separate the palladium
  9. customThereafter, the organic phase is separated
  10. washwashed with water
  11. customevaporated
  12. customCrystallization of the solid residue from toluene/hexane

Sources & evidence

ORD record
ord-d45dae448a144fef99f74b165cdbfee8
Source dataset
uspto-grants-1995_01
Patent number
US05380861

Reaction notes

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