O-Methyltyramine → HCID 58246336, compound

HRID 242099Notes

Reaction equation

HRID 242099 reaction equation
Cl.Cl[C:3]1[N:8]=[C:7]([C:9]2([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH2:26])=[CH:20][CH:19]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH:26][C:13]([C:9]2([C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][N:8]=3)[CH2:10][CH2:11][CH2:12]2)=[O:15])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 4657O-MethyltyramineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86653004HCID 86653004, compound

Product 1

HCID 58246336HCID 58246336, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(6-Chloropyridin-2-yl)cyclobutanecarboxylic acid hydrochloride (2.6 g, 10.48 mmol) was suspended in dichloromethane (30 ml). 2-(4-Methoxyphenyl)ethanamine (1.743 g, 11.53 mmol) and 4-dimethylaminopyridine (2.56 g, 20.96 mmol) were added and stirring at room temperature was continued for 30 min. The reaction mixture was cooled to 0° C. and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (2.21 g, 11.53 mmol) was added in small portions. The reaction mixture was allowed to warm to room temperature and stirring was continued over night. The reaction mixture was poured on water. The aqueous layer was extracted with dichloromethane (3×). The combined organic layers were washed with 5% aqueous citric acid and dried (MgSO4). The solvent was evaporated in vacuo and the crude product purified by flash chromatography (silica, heptane, ethyl acetate). Yield: 709 mg (2.056 mmol, 19.6%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirring
  4. waitwas continued over night
  5. additionThe reaction mixture was poured on water
  6. extractionThe aqueous layer was extracted with dichloromethane (3×)
  7. washThe combined organic layers were washed with 5% aqueous citric acid
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated in vacuo
  10. customthe crude product purified by flash chromatography (silica, heptane, ethyl acetate)

Sources & evidence

ORD record
ord-a79af92f0dd940028e6b3a9483121316
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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