4-Cyclohexylbenzenamine → 3-{4-[(4-Cyclohexylphenylamino)methyl]benzoylamino}propionic acid methyl ester

HRID 49552

Reaction equation

HRID 49552 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=1.[CH:18]1([C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:28][C:27]2[CH:29]=[CH:30][C:24]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:25][CH:26]=2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 807644-CyclohexylbenzenamineHCID 5003444Sodium cyanoborohydrideHCID 161003253-(4-Formylbenzoylamino)propionic acid methyl ester

Product 1

HCID 674839813-{4-[(4-Cyclohexylphenylamino)methyl]benzoylamino}propionic acid methyl esterYield 38.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-(4-Formylbenzoylamino)propionic acid methyl ester (10 g, 42.5 mmol) was dissolved in methanol (100 ml). With mechanical stirring 4-cyclohexylaniline (7.4 g, 42.5 mmol) was added in portions. Methanol (100 ml) was added and the resulting suspension was stirred under nitrogen at room temperature for 3 hours. Sodium cyano borohydride (4.01 g, 63.8 mmol) was added in portions and the resulting solution was stirred at room temperature for 4 days. Filtration and drying in vacuo of the formed crystals afforded 6.40 g (38%) of 3-{4-[(4-cyclohexylphenylamino)methyl]benzoylamino}propionic acid methyl ester as a solid. From the mother liquor a second crop of 2.49 g (15%) could be isolated by concentration in vacuo followed by washing with methanol.

Workup

  1. additionwas added in portions
  2. stirringthe resulting solution was stirred at room temperature for 4 days
  3. filtrationFiltration
  4. customdrying in vacuo of the formed crystals

Sources & evidence

ORD record
ord-638a319f091c4e519338a54e86022e7c
Source dataset
uspto-grants-2004_03
Patent number
US06706744B2

Linked notes

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