4-Methoxybenzaldehyde → tert-Butyl 3-(4-methoxybenzylamino)benzoate

HRID 889470Notes

Reaction equation

HRID 889470 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[NH2:11][C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=1)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].COC1C=CC(CNC2CCC2)=CC=1>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:11][C:12]2[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=2)[C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 2737408tert-Butyl-3-aminobenzoateHCID 59313984N-[(4-methoxyphenyl)methyl]cyclobutanamine

Product 1

HCID 59313743tert-Butyl 3-(4-methoxybenzylamino)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

253A was prepared from 4-methoxybenzaldehyde and tert-butyl 3-aminobenzoate following the procedure as described in 4A. HPLC: Rt=3.82 min. (PHENOMENEX® Luna C18 4.6×30 mm 3 u, A10-90% aqueous methanol containing 0.1% TFA in 2 min; 4 mL/min flow). MS (ES): m/z=314.0 [M+H]+.

Sources & evidence

ORD record
ord-e5867c0e95494768883107ddf24b9b1d
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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