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

HRID 1810035Notes

Reaction equation

HRID 1810035 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 or ganics 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 or ganics 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-05f118c596f94b64865a05455104fe1c
Source dataset
uspto-grants-2013_01
Patent number
US08362049B2

Reaction notes

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