2-Morpholinoethylamine → HCID 19003098, compound

HRID 2259322Notes

Reaction equation

HRID 2259322 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12](=O)[CH2:13][CH2:14][C:5]=3[C:4]=2[CH:3]=1.[NH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>C(#N)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:11][N:7]1[C:8]2[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][C:4]=2[C:5]2[CH2:14][CH2:13][C:12](=[N:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:6]1=2

Participants

5

Reactant 2

HCID 4082852-Morpholinoethylamine2×HCID 15818737HCID 15818737, compound

Product 1

HCID 19003098HCID 19003098, compoundYield 9.6%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 7-hydroxy-4-methyl-1,4-dihydrocyclopent[b]indol-3-one (8.00 g) in acetonitrile (125 ml) under nitrogen were added 4-(2-aminoethyl)morpholine (10.35 g) and titanium isopropoxide (22.60 g). The reaction was monitored by TLC and after two hours additional equivalents of 4-(2-aminoethyl)morpholine (5.17 g) and titanium isopropoxide (11.30 g) were added. Fourteen hours later the reaction was quenched with water (200 ml). EtOAc (200 ml) was added and the mixture stirred for fifteen minutes and filtered. The layers were separated, the aqueous layer was extracted with ethyl acetate, and the combined organics were dried (Na2SO4) and concentrated in vacuo. The resulting yellow solid was dried yielding 6.65 g. of product. A 2 g sample of the solid was further purified by crystallization from CH2Cl2 /hexane to afford 1.2 g of 4-methyl-3-[2-(4-morpholinyl)ethyl]imino-1,2,3,4-tetrahydrocyclopent[b]indol-7-ol.

Workup

  1. customFourteen hours later the reaction was quenched with water (200 ml)
  2. additionEtOAc (200 ml) was added
  3. filtrationfiltered
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe combined organics were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting yellow solid was dried
  9. customyielding 6.65 g
  10. customA 2 g sample of the solid was further purified by crystallization from CH2Cl2 /hexane

Sources & evidence

ORD record
ord-ae25fc49fdd841348edc77b98319f07e
Source dataset
uspto-grants-1995_12
Patent number
US05472975

Reaction notes

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