1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178461362, compound

HRID 1881097Notes

Reaction equation

HRID 1881097 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1.[CH:13]1[CH:14]=[CH:15][C:16]2N(O)N=[N:19][C:17]=2[CH:18]=1.[CH3:23]CN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([NH:19][C@H:17]2[CH2:18][CH2:13][C@H:14]([CH3:23])[CH2:15][CH2:16]2)=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1771643-(3-Chlorophenyl)propanoic acid

Product 1

HCID 178461362HCID 178461362, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To solution of 4-trans-methyl-cyclohexylamine hydrochloride (500 mg, 3.3 mmol) and 3-(3-chlorophenyl)propionic acid (609 mg, 3.30 mmol) in DCM (25 mL) was added HOBt (445 mg, 3.3 mmol) and EDAC (633 mg, 3.3 mmol). The mixture was stirred for 10 min at room temperature before the addition of DIPEA (1.13 mL, 6.6 mmol) and the resulting solution was stirred for a further 16 h at room temperature. DCM (25 mL) was added and the organics were washed with water (2×15 mL), 1N NaOH (10 mL), dried (MgSO4), filtered and concentrated in vacuo to yield 900 mg of 3-(3-Chloro-phenyl)-N-(trans-4-methyl-cyclohexyl)-propionamide.

Workup

  1. washthe organics were washed with water (2×15 mL), 1N NaOH (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f226f6291d6f4228927a0f3672004054
Source dataset
uspto-grants-2012_11
Patent number
US08318778B2

Reaction notes

Loading…