Triethylamine → HCID 58287247, compound

HRID 1942222Notes

Reaction equation

HRID 1942222 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][CH2:12][C:11]3([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:10]2=[O:19])=[CH:5][CH:4]=1)[CH3:2].Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[Cl:31])=[O:23].C(N(CC)CC)C>C(Cl)Cl>[Cl:31][C:25]1[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:24]=1[C:22](=[O:23])[CH2:21][N:16]1[CH2:17][CH2:18][C:11]2([C:10](=[O:19])[N:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=3)[CH2:13][CH2:12]2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 758282-Bromo-1-(2,4-dichlorophenyl)ethan-1-oneHCID 58287273HCID 58287273, compound

Product 1

HCID 58287247HCID 58287247, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

A mixture of 320 mg (1.24 mmol) 2-(4-ethylphenyl)-2,8-diazaspiro[4.5]decan-1-one, 431 mg (1.61 mmol) 2-bromo-1-(2,4-dichlorophenyl)ethanone and 376 mg (3.72 mmol) triethylamine in 50 mL DCM was stirred at 22° C. for 16 h. The crude reaction mixture was concentrated in vacuo. The crude material was purified by flash chromatography on silica eluting with a gradient formed from ethyl acetate and heptane to yield after evaporation of the product containing fractions 435 mg (79%) of the title compound as orange solid. MS m/e: 445.2 [M+H]+.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customThe crude material was purified by flash chromatography on silica eluting with a gradient
  4. customformed from ethyl acetate and heptane
  5. customto yield
  6. customafter evaporation of the product
  7. additioncontaining fractions 435 mg (79%) of the title compound as orange solid

Sources & evidence

ORD record
ord-de98c72465c84e5f92d74b460338b6c5
Source dataset
uspto-grants-2013_03
Patent number
US08389539B2

Reaction notes

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