1-Isopropylpiperazine → HCID 10144266, compound

HRID 394216Notes

Reaction equation

HRID 394216 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].[Al](C)(C)C.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[C:26]2[CH2:27][O:28][C:29](=[O:39])[N:30]([C:31]3[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:38])[C:25]=2[CH:24]=[C:23]([C:40](OC)=[O:41])[CH:22]=1.[Al]>C(Cl)Cl.C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[C:26]2[CH2:27][O:28][C:29](=[O:39])[N:30]([C:31]3[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:38])[C:25]=2[CH:24]=[C:23]([C:40]([N:7]2[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]2)=[O:41])[CH:22]=1

Participants

7

Reactant 4

HCID 780131-IsopropylpiperazineHCID 5359268AluminumHCID 16682925TrimethylaluminumHCID 22647953HCID 22647953, compound

Product 1

HCID 10144266HCID 10144266, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a dry flask charged with anhydrous CH2Cl2 (1 mL) was added 1-isopropylpiperazine (0.057 mL, 0.434 mmol, 2 eq). The mixture was cooled to 0° C. under nitrogen. To this cooled mixture was added Al(CH3)3 (0.217 mL of a 2M toluene solution, 0.434 mmol, 2 eq). After 15 min, methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,4-dihydro-2H-3,1-benzoxazine-7-carboxylate (100 mg, 0.217 mmol, 1 eq) was dissolved in CH2Cl2 (1 mL) and added to the aluminum reagent at 0° C. under nitrogen. After 2 min the cooling bath was removed. Let stir at rt for 5d. The reaction was diluted with CH2Cl2, and washed with water. The aqueous layer was back extracted 2× with CH2Cl2. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated. The product was purified by flash column chromatography on silica gel eluting with 2:1 hexanes/acetone giving 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-[(4-isopropylpiperazin-1-yl)carbonyl]-1,4-dihydro-2H-3,1-benzoxazin-2-one. Mass spectrum (ESI) 458.0 (M+1); 460 (M+3).

Workup

  1. customAfter 2 min the cooling bath was removed
  2. additionThe reaction was diluted with CH2Cl2
  3. washwashed with water
  4. extractionThe aqueous layer was back extracted 2× with CH2Cl2
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by flash column chromatography on silica gel eluting with 2:1 hexanes/acetone

Sources & evidence

ORD record
ord-e0e237c10eb2487aa5cf962b018cac20
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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