HCID 10203347, compound → HCID 10154957, compound

HRID 2265332Notes

Reaction equation

HRID 2265332 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-4ab274ab77d04a19819a647ff3b91e06
Source dataset
uspto-grants-2010_12
Patent number
US07855297B2

Reaction notes

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