Dicyclohexylamine → HCID 19911288, compound

HRID 1534082Notes

Reaction equation

HRID 1534082 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].C1(NC2CCCCC2)CCCCC1.[OH:22][N:23]1[C:27](=[O:28])[CH2:26][CH2:25][C:24]1=[O:29]>C(Cl)(Cl)Cl>[C:2](=[O:3])([O:22][N:23]1[C:27](=[O:28])[CH2:26][CH2:25][C:24]1=[O:29])[O:4][CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 62365Isobutyl chloroformateHCID 80170N-Hydroxysuccinimide

Product 1

HCID 19911288HCID 19911288, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of isobutyl chloroformate (26 ml, 200 mmole) in 600 ml of chloroform was added in portions the dicyclohexylamine (DCHA) salt of N-hydroxysuccinimide (HOSu, 49.28 g, 200 mmole). After stirring the resulting suspension overnight, the precipitated DCHA hydrochloride was filtered off and washed with chloroform. The concentrated filtrate (ca. 50 ml) and washings were diluted with 400 ml of ethyl acetate (EtOAc) and washed with 10% citric acid (4×100 ml), brine (2×100 ml), 10% sodium bicarbonate (3×100 ml), and brine (4×100 ml) and then dried (magnesium sulfate), filtered, and concentrated to ca. 100 ml. On diluting with ether and precipitating with hexane, 26.6 g (62% yield) of iBuOCO-OSu was obtained, mp 33°-35° C.

Workup

  1. filtrationthe precipitated DCHA hydrochloride was filtered off
  2. washwashed with chloroform
  3. additionThe concentrated filtrate (ca. 50 ml) and washings were diluted with 400 ml of ethyl acetate (EtOAc)
  4. washwashed with 10% citric acid (4×100 ml), brine (2×100 ml), 10% sodium bicarbonate (3×100 ml), and brine (4×100 ml)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated to ca. 100 ml
  8. additionOn diluting with ether
  9. customprecipitating with hexane

Sources & evidence

ORD record
ord-42d4132e362346618d2cfa902f23276f
Source dataset
uspto-grants-1992_02
Patent number
US05086042

Reaction notes

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