Triethylamine → HCID 178433970, compound

HRID 1867361Notes

Reaction equation

HRID 1867361 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH2:17])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(O[C:22](=[NH:24])[CH3:23])C.CCN(CC)CC>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:24][C:22]([CH3:23])=[N:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

Product 1

HCID 178433970HCID 178433970, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

4-Hydrazinocarbonyl-piperidine-1-carboxylic acid tert-butyl ester (1.19 g, 5 mmol) was mixed with ethylacetimidate hydrochloride (0.91 g, 7 mmol) in DMF (5 ml) and Et3N (2 ml, 15 mmol) was added. The reaction was stirred for 1 h after which time the DMF was evaporated, the residue redissolved in AcOH and 0.5 g of ammonium acetate added and the reaction heated to 100° C. for a further 3 h. The reaction was then concentrated, redissolved in CH2Cl2, washed with NaHCO3, dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (CH2Cl2:MeOH 1:0-9:1) to afford the title product (0.14 g, 10%) as a colourless gum. MS: 267.4 (MH+)

Workup

  1. additionwas added
  2. customwas evaporated
  3. dissolutionthe residue redissolved in AcOH
  4. addition0.5 g of ammonium acetate added
  5. concentrationThe reaction was then concentrated
  6. dissolutionredissolved in CH2Cl2
  7. washwashed with NaHCO3
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue was purified by flash column chromatography (CH2Cl2:MeOH 1:0-9:1)

Sources & evidence

ORD record
ord-f72a68f57a1d4ffb8f6635c9348bfa5a
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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