1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(1-(3-Amino-4-methylbenzoyl)piperidin-4-yl)benzonitrile

HRID 541242Notes

Reaction equation

HRID 541242 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.Cl.[NH:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH2:15][CH2:14]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)=[O:7]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 755683-Amino-4-methylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 193916184-(Piperidin-4-yl)benzonitrile--hydrogen chloride (1/1)2×

Product 1

HCID 576669154-(1-(3-Amino-4-methylbenzoyl)piperidin-4-yl)benzonitrileYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-amino-4-methylbenzoic acid (1.36 g, 9.0 mmol), (4-(piperidin-4-yl)benzonitrile HCl salt (compound 1.5, 2.0 g, 9.0 mmol), EDCI (1.89 g, 9.9 mmol), HOBT (1.66 g, 9.9 mmol, with 20% H2O) and DIEA (3.13 ml, 18.0 mmol) in DMF (50 ml) was stirred at room temperature overnight. The reaction mixture was poured into cold water (300 ml) and off white solids precipitated. The precipitate was filtered, washed with water and dried under reduced pressure in an oven to yield 2.88 g (100%) of the title compound. m/z (ES+) 320 (M+H)+.

Workup

  1. customprecipitated
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried under reduced pressure in an oven

Sources & evidence

ORD record
ord-625b409507d9412788edbb84816e3da3
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

Loading…