Benzocaine → Ethyl 4-[[4-(dimethylamino)phenyl]methylamino]benzoate

HRID 131287Notes

Reaction equation

HRID 131287 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][N:14]([CH3:23])[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:13][N:14]([CH3:23])[C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 2337BenzocaineHCID 74794-(Dimethylamino)BenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 3243284Ethyl 4-[[4-(dimethylamino)phenyl]methylamino]benzoateYield 64.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-aminobenzoate (10 g) and 4-(dimethylamino)benzaldehyde (9.0 g) in methylene chloride (200 mL) is added sodium triacetoxyborohydride (18.9 g) and acetic acid (3.47 mL) under ice-cooling, and the mixture is stirred at room temperature for 2 days. To the reaction mixture is added a saturated sodium hydrogencarbonate solution and extracted with chloroform (×2). The extract is concentrated in vacuo and the residue is triturated in n-hexane/ethyl acetate to give ethyl 4-[4-(dimethylamino)benzylamino]benzoate (11.6 g, yield; 64%) as powder. MS (APCI) m/z; 299 [M+H]+

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform (×2)
  3. concentrationThe extract is concentrated in vacuo
  4. customthe residue is triturated in n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-e4f69942d76f4fa4aafdefbbf6869db6
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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