Hydrochloric Acid → 3,3-Dimethyl-6-morpholinoindoline

HRID 1618482Notes

Reaction equation

HRID 1618482 reaction equation
[CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[N:4](C(=O)C)[CH2:3]1.Cl.C([O-])(O)=O.[Na+]>C(#N)C>[CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[NH:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 672845771-(3,3-Dimethyl-6-morpholinoindolin-1-yl)ethanone

Product 1

HCID 672848583,3-Dimethyl-6-morpholinoindoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3,3-Dimethyl-6-morpholinoindolin-1-yl)ethanone was dissolved in acetonitrile (100 mL) and treated with 5 N HCl (50 mL) at 95° C. After 2 h, the mixture was cooled to rt. The reaction was carefully neutralized with saturated NaHCO3 solution to pH 10 and extracted with EtOAc (100 mL×4). The combined organics were washed with water, brine, dried, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/hexane, 0/1 to 1/0) to give 4-(3,3-dimethylindolin-6-yl)morpholine as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 6.80 (1H, d, J=7.8 Hz), 6.14 (1H, dd, J=8.0, 2.2 Hz), 6.09 (1H, d, J=2.0 Hz), 5.28 (1H, s), 3.65-3.73 (4H, m), 3.13 (2H, d, J=2.0 Hz), 2.92-2.99 (4H, m), 1.17 (6H, s). Mass Spectrum (ESI) m/e=233.2 (M+1).

Workup

  1. extractionextracted with EtOAc (100 mL×4)
  2. washThe combined organics were washed with water, brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (EtOAc/hexane, 0/1 to 1/0)

Sources & evidence

ORD record
ord-b997c6d32f0b4a3ab8bbed052ba026d1
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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