Dimethylformamide → HCID 67897260, compound

HRID 1651626Notes

Reaction equation

HRID 1651626 reaction equation
[CH3:1][C:2]12[CH:17]([CH3:18])[CH:15]3[NH:16][C:11]4[CH:12]([CH2:14]3)[CH2:13][C:4](=[C:5]([CH:10]=4)[CH:6]=[CH:7][CH2:8][NH:9]1)[CH2:3]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][CH:14]2[CH:12]3[CH2:13][C:4]4[CH2:3][C:2]5([CH3:1])[CH:17]([CH3:18])[CH:15]2[NH:16][C:11]3=[CH:10][C:5]=4[CH:6]=[CH:7][CH2:8][NH:9]5)[CH2:35][CH2:34]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81503BromomethylcyclopropaneHCID 81531DiisopropylethylamineHCID 73656241HCID 73656241, compound

Product 1

HCID 67897260HCID 67897260, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 0.99 g of 6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-8H-pyrrolo[2,3-i][3]benzazocine and 18 ml of dimethylformamide was added 1.44 ml of diisopropylethyl amine. Cyclopropylmethyl bromide (0.48 ml) was added, under nitrogen, and the reaction mixture was heated at 82°-83° C. for 6 hr. The reaction mixture was cooled to room temperature and was poured into ethyl acetate and water. The layers were separated and the aqueous layer extracted with ethyl acetate and ether. The combined organic layers were washed with water and brine, dried over anhydrous potassium carbonate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 2% triethylamine/0-15% methanol/ethyl acetate), a second column (silica gel, 2% triethylamine/ethyl acetate), and a third column (silica gel, 1% triethylamine/ether) to afford 0.28 g (23%) of the product, as an oil, which crystallized upon trituration with ether. Recrystallization from ether-pentane gave the analytical sample, mp 164°-166° C.

Workup

  1. temperaturethe reaction mixture was heated at 82°-83° C. for 6 hr
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with ethyl acetate and ether
  4. washThe combined organic layers were washed with water and 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/0-15% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-7b344f32b2614effb4d0586fa9968b5c
Source dataset
uspto-grants-1990_05
Patent number
US04929622

Reaction notes

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