Dimethylformamide → HCID 73656237, compound

HRID 2248122Notes

Reaction equation

HRID 2248122 reaction equation
[CH3:1][C:2]12[CH:17]([CH3:18])[CH:15]3[NH:16][C:12]4=[C:13]([CH2:14]3)[C:8](=[C:9]1[CH2:10][CH2:11]4)[CH:7]=[CH:6][NH:5][CH:4]=[CH:3]2.CN(C)C=O.C(N(C(C)C)CC)(C)C.[CH:33]1([CH2:36]Br)[CH2:35][CH2:34]1>O.C(OCC)(=O)C>[CH:33]1([CH2:36][N:16]2[C:12]3[CH2:11][CH2:10][C:9]4[C:2]5([CH3:1])[CH:17]([CH3:18])[CH:15]2[CH2:14][C:13]=3[C:8]=4[CH:7]=[CH:6][NH:5][CH:4]=[CH:3]5)[CH2:35][CH2:34]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81503BromomethylcyclopropaneHCID 81531DiisopropylethylamineHCID 73656238HCID 73656238, compound

Product 1

HCID 73656237HCID 73656237, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2.05 g of 6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo[2,3-j][3]benzazocine and 37 ml of dimethylformamide was added 2.23 ml of diisopropylethyl amine. Cyclopropylmethyl bromide (0.91 ml) was added, under nitrogen, and the reaction mixture was heated at 73°-75° C. for 3.75 hr. The mixture was cooled to room temperature and poured into ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate and ether. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate) to afford 1.48 g (59%) of product. Recrystallization from ether gave the analytical sample, mp 151.5°-153.5° C.

Workup

  1. temperaturethe reaction mixture was heated at 73°-75° C. for 3.75 hr
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate and ether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate)

Sources & evidence

ORD record
ord-b35afd91d7fc41f0a3af37752f7e6f64
Source dataset
uspto-grants-1991_08
Patent number
US05037985

Reaction notes

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