Potassium Carbonate → 4-[(4-Cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl ester

HRID 1633916

Reaction equation

HRID 1633916 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:20]1(=[C:23]2[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]2)[CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCC(Cl)C.ClCCl.C(O)(=O)C>[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][CH:26]2[CH2:27][CH2:28][C:23](=[C:20]3[CH2:22][CH2:21]3)[CH2:24][CH2:25]2)=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 225021744-Cyclopropylidenecyclohexanone

Product 1

HCID 235501404-[(4-Cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl esterYield 35%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×HCID 65641,2-DichloropropaneSolvent

Procedure

4-Aminomethylbenzoic acid methyl ester, hydrochloride salt (2.2 g, 11 mmol) was suspended in 1,2 dichloropropane (30 mL) and an aqueous saturated solution of potassium carbonate (15 mL) was added. The next day the organic phase was isolated and dried (MgSO4). 4-Cyclopropylidenecyclohexanone (1.5 g, 11 mmol) dissolved in dichloromethane (15 mL) was added followed by addition of acetic acid (400 μL) and sodium triacetoxyborohydride (3.3 g, 16.5 mmol). After 72 hours at 20° C. the reaction mixture was diluted with dichloromethane (50 mL) and washed with aqueous saturated sodium hydrogen carbonate (2×30 mL) and water (5×30 mL). The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (50 g silica) using ethyl acetate and methanol (97:3) as eluent to give 1.1 g of 4-[(4-cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl ester.

Workup

  1. customThe next day the organic phase was isolated
  2. dry with materialdried (MgSO4)
  3. additionwas added
  4. washwashed with aqueous saturated sodium hydrogen carbonate (2×30 mL) and water (5×30 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (50 g silica)

Sources & evidence

ORD record
ord-845f7342b41040548f9c4870cf589567
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Linked notes

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