N,N,N',N'-Tetramethyl-1,3-diaminopropane → Methyl 4-(((4'-chlorobiphenyl-4-yl)(cyclohexyl)methyl)amino)benzoate

HRID 1520291Notes

Reaction equation

HRID 1520291 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CN(C)CCCN(C)C.CS(Cl)(=O)=O.[NH2:36][C:37]1[CH:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][CH:38]=1.C(N(CC)C(C)C)(C)C>O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([NH:36][C:37]3[CH:38]=[CH:39][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:45][CH:46]=3)[CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 8084N,N,N',N'-Tetramethyl-1,3-diaminopropaneHCID 12082Methyl 4-aminobenzoateHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 117839871(4'-Chlorobiphenyl-4-yl)(cyclohexyl)methanol

Product 1

HCID 118105508Methyl 4-(((4'-chlorobiphenyl-4-yl)(cyclohexyl)methyl)amino)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, to a mixture of (4′-chlorobiphenyl-4-yl)(cyclohexyl)methanol obtained in step B, N,N,N′,N′-tetramethyl-1,3-propanediamine (0.265 mL) and toluene (4.432 mL) was added methanesulfonyl chloride (0.124 mL) at 0° C., and the reaction mixture was stirred at room temperature for 4 hr. To the reaction mixture were added methyl 4-aminobenzoate (301 mg) and N,N-diisopropylethylamine (0.464 mL) at room temperature, and the mixture was stirred at 100° C. overnight. To the reaction mixture was added water at room temperature, the mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (382.4 mg).

Workup

  1. stirringthe mixture was stirred at 100° C. overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-88a1cb3a9fef4baa8517cebdf6ee2ed7
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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