N-(3-Aminopropyl)morpholine → HCID 13670193, compound

HRID 746203Notes

Reaction equation

HRID 746203 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.Cl[S:12]([C:15]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:16]=1[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:13]>C1COCC1>[O:8]1[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH2:2][NH:1][S:12]([C:15]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:16]=2[C:17]([O:19][CH3:20])=[O:18])(=[O:13])=[O:14])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 13670189Methyl 2-(chlorosulfonyl)-6-nitrobenzoate

Product 1

HCID 13670193HCID 13670193, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(3-aminopropyl)morpholine (1.04 g, 7.2 mmol) in THF (25 ml) was added slowly to a cooled solution of methyl 2-chlorosulfonyl-6-nitrobenzoate (1.0 g, 3.6 mmol) in THF (75 ml). After stirring at 20°-25° C. for 20 hours, THF was removed under reduced pressure and the residue partitioned between EtOAc and a saturated aqueous solution of NaCl. The EtOAc extract was dried (Na2SO4), filtered and concentrated. Flash chromatography of the residue and elution with 2% MeOH-98% CHCl3 gave 1.4 g of product as an oil.

Workup

  1. customTHF was removed under reduced pressure
  2. customthe residue partitioned between EtOAc
  3. extractionThe EtOAc extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washFlash chromatography of the residue and elution with 2% MeOH-98% CHCl3

Sources & evidence

ORD record
ord-f456ccc56a884c28bf53760118fa8d0f
Source dataset
uspto-grants-1986_07
Patent number
US04603133

Reaction notes

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