HCID 10203347, compound → HCID 10154957, compound

HRID 218563Notes

Reaction equation

HRID 218563 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:23][CH2:24][CH2:25][O:26]C2CCCCO2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]>C(O)(=O)C.C1COCC1.O>[OH:26][CH2:25][CH2:24][CH2:23][N:10]([C:7]1[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=1)[C:11]([CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1)=[O:12]

Participants

3

Reactant 1

HCID 10203347HCID 10203347, compound

Product 1

HCID 10154957HCID 10154957, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

N-(4-Isopropylphenyl)-N-[3-(tetrahydropyran-2-yloxy)propyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.24 g) was dissolved in a mixed solvent (7 mL) of acetic acid: THF: water (4:2:1) and stirred at room temperature for 2 hr. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give N-(3-hydroxypropyl)-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.12 g).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2eb1a2442c09403e9a6d203bbc0beccd
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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