4-Methylmorpholine → HCID 68885273, compound

HRID 1743945Notes

Reaction equation

HRID 1743945 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][C:11](=[O:13])[CH2:10][C@H:9]2[C:14]([OH:16])=O)=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[Cl-].[CH:47]1([C:53]2([CH2:59][N:60]3[C:64]([CH3:66])([CH3:65])[CH2:63][O:62][C:61]3=[O:67])[CH2:58][CH2:57][NH2+:56][CH2:55][CH2:54]2)[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:12][C:11](=[O:13])[CH2:10][C@H:9]2[C:14]([N:56]2[CH2:57][CH2:58][C:53]([CH2:59][N:60]3[C:64]([CH3:65])([CH3:66])[CH2:63][O:62][C:61]3=[O:67])([CH:47]3[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]3)[CH2:54][CH2:55]2)=[O:16])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17980475HCID 17980475, compoundHCID 68517764HCID 68517764, compound

Product 1

HCID 68885273HCID 68885273, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 25 mL round bottom flask equipped with a magnetic stir bar was charged with 0.412 g (1.73 mmol) of the product of Step D dissolved in 6 mL of methylene chloride. To the reaction mixture was added 0.451 g (2.35 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.318 g (2.35 mmol) of 1-hydroxybenzotriazole, 0.518 μL (4.71 mmol) of N-methylmorpholine, followed by 0.520 g (1.57 mmol) of 4-cyclohexyl-4-[(4,4-dimethyl-2-oxo-1,3-oxazolidin-3-yl)methyl]piperidinium chloride. The resulting clear yellow solution was stirred at room temperature for 48 h, then was partitioned between methylene chloride and saturated aqueous sodium bicarbonate. The organic layer was separated, washed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate, brine, then dried (Na2SO4), filtered and evaporated in vacuo. The residual oil was purified on a Biotage Flash 40i chromatography apparatus (40 g Flash 40S silica gel cartridge) eluted sequentially with hexane for 2 min, 30% ethyl acetate-hexanes for 2 min and finally 75% ethyl acetate-hexanes for 20 min. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Workup

  1. customA 25 mL round bottom flask equipped with a magnetic stir bar
  2. customwas partitioned between methylene chloride and saturated aqueous sodium bicarbonate
  3. customThe organic layer was separated
  4. washwashed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residual oil was purified on a Biotage Flash 40i chromatography apparatus (40 g Flash 40S silica gel cartridge)
  9. washeluted sequentially with hexane for 2 min
  10. wait30% ethyl acetate-hexanes for 2 min
  11. waitfinally 75% ethyl acetate-hexanes for 20 min
  12. customEvaporation of the purified fractions
  13. customdrying in vacuo

Sources & evidence

ORD record
ord-10d72f3f25734906806deb157a6ebc4c
Source dataset
uspto-grants-2006_03
Patent number
US07012084B2

Reaction notes

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