Methylparaben → Methyl 4-(2-cyclopropylaminoethoxy)benzoate

HRID 354517Notes

Reaction equation

HRID 354517 reaction equation
[CH:1]([CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)=O.OC1C=CC(C(OC)=O)=CC=1.[CH:26]1([NH2:29])[CH2:28][CH2:27]1.[BH3-]C#N.[Na+]>CO.CC(O)=O>[CH:26]1([NH:29][CH2:1][CH2:3][O:4][C:5]2[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][CH:14]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 11636984methyl 4-formylmethyloxybenzoate

Product 1

HCID 23512183Methyl 4-(2-cyclopropylaminoethoxy)benzoateYield 49%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

To a stirred solution of 4:1 mixture of methyl 4-formylmethyloxybenzoate and methyl 4-hydroxybenzoate (1.00 g) and cyclopropylamine (425 ml, 6.18 mmol) in MeOH—AcOH (10:1, 11 ml) was added NaBH3CN (681 mg, 10.3 mmol). After stirring overnight, the mixture was quenched by addition of sat. NaHCO3 (50 ml) and extracted with CHCl3 (2×200 ml). The combined extracts were dried over MgSO4 and evaporated. The residue was chromatographed on silica gel with CHCl3—MeOH (20:1) to give methyl 4-(2-cyclopropylaminoethoxy)benzoate (595 mg, 49%) as a colorless oil. 1H-NMR (CDCl3) δ0.37-0.49 (m, 4 H), 1.91 (m, 1 H), 2.18-2.23 (m, 1 H), 3.11 (t, J=5.2 Hz, 2 H), 3.88 (s, 3 H), 4.12 (t, J=5.2 Hz, 2 H), 6.92 (, J=8.88 Hz, 2 H), 7.98 (d, J=8.8 Hz, 2 H).

Workup

  1. customthe mixture was quenched by addition of sat. NaHCO3 (50 ml)
  2. extractionextracted with CHCl3 (2×200 ml)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. customevaporated
  5. customThe residue was chromatographed on silica gel with CHCl3—MeOH (20:1)

Sources & evidence

ORD record
ord-889e565613304bba99d880b08f04dd25
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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