1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58732681, compound

HRID 553001Notes

Reaction equation

HRID 553001 reaction equation
[CH3:1][CH:2]1[CH2:11][CH:10]([C:12](O)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:15](=[O:26])[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1.[CH2:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)[CH3:28].CCN=C=NCCCN(C)C.O.[Cl-].[Na+].O>N1C=CC=CC=1>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([N:29]([CH2:27][CH3:28])[C:12]([C@@H:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]([C:15](=[O:26])[C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:20][CH:21]=3)[C@@H:2]([CH3:1])[CH2:11]2)=[O:13])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 5878414-chloro-N-ethylanilineHCID 23713072Sodium chloride dihydrateHCID 67164698HCID 67164698, compound

Product 1

HCID 58732681HCID 58732681, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A round bottom flask with magnetic stirrer was charged with 2-methyl-1-(4-trifluoromethyl-benzoyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (886 mg, 2.44 mmol) in anhydrous pyridine (25.0 mL). To the reaction was added N-ethyl-p-chloroaniline (0.410 mL, 2.95 mmol), followed by EDCI (833 mg, 4.34 mmol). The reaction was stirred at room temperature under an argon atmosphere for 18-20 hours. The reaction was poured into a 1:1 mixture of water/brine (50 mL) and extracted with ethyl acetate (3×35 mL). The combined extractions were washed with brine (1×50 mL), dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to afford a brown residue. The residue was purified via silica gel chromatography (hexanes/ethyl acetate) to yield (±)-trans-2-methyl-1-(4-trifluoromethyl-benzoyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide (39%). 1H-NMR (CDCl3) δ: 1.02 (d, 3H), 1.12 (t, 3H), 1.64-1.74 (m, 1H), 2.49-2.58 (m, 1H), 3.59-3.72 (m, 1H), 3.77-3.90 (m, 2H), 5.03-5.14 (m, 1H), 6.35-6.41 (m, 1H), 6.74-6.84 (m, 2H), 6.89-6.95 (m, 1H), 7.17-7.25 (m, 2H), 7.44-7.52 (m, 2H), 7.63-7.69 (m, 2H). MS m/z: 501 (M+1).

Workup

  1. extractionextracted with ethyl acetate (3×35 mL)
  2. extractionThe combined extractions
  3. washwere washed with brine (1×50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto afford a brown residue
  8. customThe residue was purified via silica gel chromatography (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-1c73802878c8474e9bb649bd00f565f0
Source dataset
uspto-grants-2011_05
Patent number
US07951950B2

Reaction notes

Loading…