Acetic Acid → HCID 16067949, compound

HRID 480370Notes

Reaction equation

HRID 480370 reaction equation
[C:1]1([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=O.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CO.C(OCC)(=O)C>[CH3:23][O:22][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][C:16]([CH2:14][NH:11][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=3)=[CH:13][CH:12]=2)=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 15294Methyl 4-FormylbenzoateHCID 5049666Sodium triacetoxyborohydrideHCID 126688602',3',4',5'-Tetrahydro-[1,1'-biphenyl]-4-amine

Product 1

HCID 16067949HCID 16067949, compoundYield 65.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-cyclohexenylaniline (3,40 g, 0.023 mol) and methyl 4-formylbenzoate (3.77 g, 0.023 mol) in DCM (50 ml) and methanol (15 ml) was added a catalytic amount of acetic acid. After stirring the solution for 3 hours, Na(OAc)3BH (24 g, 0.115 mol) was added. The reaction was allowed to stir at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate (3×), brine (2×), dried over magnesium sulphate, filtered, and concentrated to give an orange solid. The crude product was introduced into a column of silica gel and eluted with ethyl acetate:hexane (5:95) to give 4-[(4-cyclohex-1-enylphenylamino)methyl]benzoic acid methyl ester (5 g, 0.015 mol).

Workup

  1. stirringto stir at room temperature for 16 hours
  2. washwashed with aqueous sodium bicarbonate (3×), brine (2×)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an orange solid
  7. washeluted with ethyl acetate:hexane (5:95)

Sources & evidence

ORD record
ord-3b7ad99bba784c469779f22a5654a860
Source dataset
uspto-grants-2003_11
Patent number
US06649641B2

Reaction notes

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