Hydrochloric Acid → 3-phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate cyclohexylamide

HRID 17897

Reaction equation

HRID 17897 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:13][CH:14]=3)[C:9](=[O:26])[C:8]=2[C:27]([O-:29])=[O:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH:37]1([NH2:43])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.Cl>ClCCl.O>[CH:37]1([NH-:43])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:13][CH:14]=3)[C:9](=[O:26])[C:8]=2[C:27]([O-:29])=[O:28])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7965CyclohexylamineHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 866140333-Phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate

Product 1

HCID 866140323-phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate cyclohexylamideYield 59.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-Phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate (200 mg, 0.52 mmol) was dissolved in dichloromethane (10 ml). Triethylamine (240 μl, 1.72 mmol) and cyclohexylamine (59 μl, 0.52 mmol) were added thereto at 10° C. Then, after adding bis(2-oxo-3-oxazolidinyl)phosphinic chloride (137 mg, 0.52 mmol), the reaction mixture was stirred for about 20 min at room temperature followed by additional 1 hour at 10° C. After the water was added thereto to complete the reaction, pH was adjusted to 1˜1.5 with 4N hydrochloric acid. The mixture was washed with brine, and extracted with dichloromethane. The extract was dried over anhydrous sulfonate sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:9˜2:8) to obtain the title compound (yield 59.8%) as a red solid.

Workup

  1. customat 10° C
  2. waitfollowed by additional 1 hour at 10° C
  3. customthe reaction, pH
  4. washThe mixture was washed with brine
  5. extractionextracted with dichloromethane
  6. dry with materialThe extract was dried over anhydrous sulfonate sulfate
  7. concentrationconcentrated
  8. customthe resulting residue was purified by column chromatography (ethyl acetate:hexane=1:9˜2:8)

Sources & evidence

ORD record
ord-b7a74c8b2c8249d2bb1e621f9135b741
Source dataset
uspto-grants-2010_06
Patent number
US07741323B2

Linked notes

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