1-(4-Chlorophenyl)-2-(1-imidazolidinyl)-4-methyl-3-hexanone → HCID 66757906, compound

HRID 1983802Notes

Reaction equation

HRID 1983802 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([N:16]2[CH2:20][CH2:19][NH:18][CH2:17]2)[C:10](=[O:15])[CH:11]([CH3:14])[CH2:12][CH3:13])=[CH:4][CH:3]=1.Br[CH2:22][CH2:23][CH:24]=[C:25]1[C:31]2[CH:32]=[CH:33][CH:34]=[N:35][C:30]=2[CH2:29][O:28][C:27]2[CH:36]=[CH:37][C:38]([C:40]([OH:43])([CH3:42])[CH3:41])=[CH:39][C:26]1=2>C(O)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([N:16]2[CH2:20][CH2:19][N:18]([CH2:22][CH2:23][CH:24]=[C:25]3[C:31]4[CH:32]=[CH:33][CH:34]=[N:35][C:30]=4[CH2:29][O:28][C:27]4[CH:36]=[CH:37][C:38]([C:40]([OH:43])([CH3:42])[CH3:41])=[CH:39][C:26]3=4)[CH2:17]2)[C:10](=[O:15])[CH:11]([CH3:14])[CH2:12][CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 184370381-(4-Chlorophenyl)-2-(1-imidazolidinyl)-4-methyl-3-hexanoneHCID 666859992-[5-(3-Bromo-propylidene)-5,1 1-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol

Product 1

HCID 66757906HCID 66757906, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
77 °C

Procedure

To a heated (77° C.) stirring solution of 1-(4-chloro-phenyl)-2-imidazolidin-1-yl-4-methyl-hexan-3-one (110 mg, 0.374 mmol), 2,6-lutidiene (130 μL, 11.229 mmol) and 5 mL isopropanol was added 2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (70 mg, 0.187 mmol) portion-wise over a 30 minute period. The resulting solution was monitored using thin layer chromatography and allowed to stir at 77° C. for 16 hours. The solution was concentrated in vacuo at 35° C. The residue was dissolved in ethyl acetate and subjected to column chromatography (SiO2, Biotage 12M column, gradient elution 100% ethyl acetate→92% ethyl acetate/8% methanol with 1% triethyl amine) to afford 54 mg of 1-(4-chloro-phenyl)-2-(3-{3-[7-(1-hydroxy-1-methyl-ethyl)-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene]-propyl}-imidazolidin-1-yl)-4-methyl-hexan-3-one as a tan foam. LC/MS: tUV=1.68 min, M/Z=588 amu.

Workup

  1. concentrationThe solution was concentrated in vacuo at 35° C
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washsubjected to column chromatography (SiO2, Biotage 12M column, gradient elution 100% ethyl acetate→92% ethyl acetate/8% methanol with 1% triethyl amine)

Sources & evidence

ORD record
ord-6bc6ed5241f44d0dbdbd1f7466a50fc0
Source dataset
uspto-grants-2009_06
Patent number
US07541365B2

Reaction notes

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