1,2-Dichloroethane → HCID 178520485, compound

HRID 1884514Notes

Reaction equation

HRID 1884514 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[NH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([NH:13][C@H:14]2[CH2:15][CH2:16][C@H:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][CH2:19]2)=[O:12])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 103943-(4-Hydroxyphenyl)propionic acidHCID 757711-HydroxybenzotriazoleHCID 178511499HCID 178511499, compound

Product 1

HCID 178520485HCID 178520485, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(4-hydroxyphenyl)propionic acid 7 (0.48 g, 2.9 mmol), amine 5 (0.50 g, 2.9 mmol), EDC (0.67 g, 3.5 mmol), and HOBT (0.39 g, 2.9 mmol) in DMF (5 mL) was stirred under an atmosphere of nitrogen overnight. The reaction mixture was partitioned between H2O (25 mL) and EtOAc (50 mL). The organic layer was washed with H2O, 3N HCl (25 mL), H2O (25 mL), and saturated NaCl (25 mL). After drying (Na2SO4), concentration under reduced pressure gave (a) trans-3-(4-hydroxyphenyl)-N-(4-phenylcyclohexyl)propionamide (0.65 g, 69%) which was used without further purification: 1H NMR (300 MHz, CD3OD) δ 7.28-7.06 (m, 5H), 3.74-3.60 (m, 1H), 2.80 (t, J=4 Hz, 2H), 2.51-2.36 (m, 3H), 1.97-1.82 (m, 4H), 1.67-1.51 (m, 2H), 1.40-1.21 (m, 2H).

Workup

  1. customThe reaction mixture was partitioned between H2O (25 mL) and EtOAc (50 mL)
  2. washThe organic layer was washed with H2O, 3N HCl (25 mL), H2O (25 mL), and saturated NaCl (25 mL)
  3. customAfter drying
  4. concentration(Na2SO4), concentration under reduced pressure

Sources & evidence

ORD record
ord-8bcb8e6c969f43e8ae0a828a34ab4802
Source dataset
uspto-grants-2004_07
Patent number
US06765022B2

Reaction notes

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