Dimethylformamide → HCID 53752137, compound

HRID 1651618Notes

Reaction equation

HRID 1651618 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][CH2:5][N: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>C(OCC)(=O)C.O>[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][CH2:5][N:4]=[CH:3]5)[CH2:35][CH2:34]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81503BromomethylcyclopropaneHCID 81531DiisopropylethylamineHCID 73656243HCID 73656243, compound

Product 1

HCID 53752137HCID 53752137, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3.22 g of 1,2,3,4,5,6-hexahydro-6,12-dimethyl-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine and 58 ml of dimethylformamide was added 4.70 ml of diisopropylethyl amine and then 1.56 ml of cyclopropylmethyl bromide, under nitrogen. The reaction mixture was warmed in an oil bath at 70°-80° C. for 1.5 hr and stirred at room temperature overnight. The reaction mixture was poured into water and ethyl acetate. 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 the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, 2% triethylamine/0-10% methanol/ethyl acetate) gave 2.48 g (63%) of product. Sublimation (173°-175° C., ~0.3 mm) gave the analytical sample, mp 187°-190° C. (dec).

Workup

  1. temperatureThe reaction mixture was warmed in an oil bath at 70°-80° C. for 1.5 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. concentrationthe filtrate was concentrated
  8. customThe residue was purified by flash column chromatography (silica gel, 2% triethylamine/0-10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-f477a1bd22a143b99fc66e57f9947418
Source dataset
uspto-grants-1990_05
Patent number
US04929622

Reaction notes

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