Triethylamine → HCID 86586628, compound

HRID 1359588Notes

Reaction equation

HRID 1359588 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH2:9][CH:8](CCN)[C:7]=2[CH:14]=1)#[N:2].CC[N:17](CC)CC.[C:22]1([C:28]2[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH2:9][CH:8]([C:35]3[CH:36]=[C:28]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:29]=[CH:30][C:31]=3[C:32]([NH2:17])=[O:33])[C:7]=2[CH:14]=1)#[N:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 18182564HCID 18182564, compound

Product 1

HCID 86586628HCID 86586628, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled (0° C.) solution of 2-(5-cyano-2,3-dihydro-benzofuran-3-yl)-ethyl amine (reference example 6, 382 mg, 2 mmol) in CH2Cl2 (9 mL) is added Et3N (0.55 mL, 4 mmol) followed by 4-phenyl-benzoyl chloride (440 mg, 2.03 mmol). The resulting solution is stirred for 15 min. then diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (50% ethyl acetate/10% CH2Cl2 in hexanes) to give the title compound (476 mg) as a solid 1H NMR (CDCl3) d 1.96 (m, 1H), 2.10 (m, 1H), 3.50-3.70 (m, 3H), 4.50 (dd, J=9, 8 Hz, 1H), 4.83 (t, J=9 Hz, 1H), 6.31 (bt, 1H), 6.86 (d, J=8 Hz, 1H), 7.37-7.59 (m, 5H), 7.6-7.75 (m, 4H), 7.85 (d, J=8 Hz, 2H). MS (EI) m/z 368 (M)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue is purified by flash chromatography (50% ethyl acetate/10% CH2Cl2 in hexanes)

Sources & evidence

ORD record
ord-d8d41e8445264049aa72ebd5d856d601
Source dataset
uspto-grants-2003_07
Patent number
US06599918B2

Reaction notes

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