Triethylamine → HCID 178484805, compound

HRID 1161354Notes

Reaction equation

HRID 1161354 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[C:20]([O:23][CH2:24][CH3:25])(=[O:22])[CH3:21].[CH3:26][CH2:27][CH2:28][CH2:29]CC>C(Cl)Cl>[CH2:24]([O:23][C:20](=[O:22])[CH2:21][C@H:27]1[CH2:26][CH2:7][C@H:6]([N+:3]#[C-:4])[CH2:29][CH2:28]1)[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 21226206Ethyl acetate hexane

Product 1

HCID 178484805HCID 178484805, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

5 g (22.8 mmol) of trans-(4-Amino-cyclohexyl)-acetic acid ethyl ester hydrochloride were suspended in a mixture of 40 ml (731 mmol) ethylformiate and 10 ml DMF. 5.6 ml (25 mmol) of DIPEA were added and the mixture was heated to 80° C. for 72 h. The solvent mixture was evaporated to dryness and the crude product extracted from ethyl acetate/water. 4.2 g of a yellow solid were obtained which were dissolved in 40 ml DCM. 6.6 ml (47 mmol) triethylamine were added and the mixture was cooled to 0-5° C. 2.3 ml (7.9 mmol) of triphosgene were dissolved in 10 ml DCM and added dropwise. The reaction mixture was warmed to room temperature and the product was isolated directly via silica gel chromatography using ethyl acetate/hexane as an eluant. The intermediate was used without further characterization.

Workup

  1. additionadded dropwise
  2. temperatureThe reaction mixture was warmed to room temperature
  3. customthe product was isolated directly via silica gel chromatography

Sources & evidence

ORD record
ord-4081ede1d3da4047add1a8514a4bd57e
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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