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Water → HCID 69659103, compound

HRID 1829044
Notes
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Reaction equation

HRID 1829044 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH3:24])[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[C:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]1=[O:23])[O:9][CH2:8]2.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.O>CN(C=O)C>[CH3:24][N:4]([CH2:3][CH2:2][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[C:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]1=[O:23])[O:9][CH2:8]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 69659015HCID 69659015, compound

Product 1

HCID 69659103HCID 69659103, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-{5-[(2-chloro-ethyl)-methyl-amino]-3H-isobenzofuran-1-ylidene}-1,3-dihydro-indol-2-one (1.20 g, 3.52 mmol) and morpholine (3 ml, 34.4 mmol) in DMF (5 ml) was heated at 110° C. under nitrogen for 16 hours. The mixture was cooled to room temperature and was then poured into water (100 ml). The solid was filtered, washed with water and dried under vacuum to give a crude product. Purification of the crude product by silica gel column chromatography, eluted with a gradient of MeOH in CHCl3, resulted in 3-{5-[methyl-(2-morpholin-4-yl-ethyl)-amino]-3H-isobenzofuran-1-ylidene}-1,3-dihydro-indol-2-one as a yellow solid (0.57 g, 41%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried under vacuum
  5. customto give a crude product
  6. customPurification of the crude product by silica gel column chromatography
  7. washeluted with a gradient of MeOH in CHCl3
  8. customresulted in 3-{5-[methyl-(2-morpholin-4-yl-ethyl)-amino]-3H-isobenzofuran-1-ylidene}-1,3-dihydro-indol-2-one as a yellow solid (0.57 g, 41%)

Sources & evidence

ORD record
ord-fee7afabbdca4725bbb341c7c2183a5f
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07060844B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes